


World Tour

by AmeliaSPN1973



Category: Supernatural
Genre: AU, Busty Asian Beauties, Cocky, Date Rape, Dean is a musician, Dopplegangers, F/M, Fighting, Friendship, Grammy Awards, Groupies, Infidelity, Living Together, Love, Making Up, Meeting Your Idols, Mile High Club, Moving In Together, No Privacy, Not Beta Read, Pregnancy, Romance, Roofies, Sex, Smut, Stalker, Touring, Violence, You first dislike him, dubcon, living on a bus, non con, world tour
Language: English
Status: Completed
Published: 2019-10-17
Updated: 2019-10-17
Packaged: 2020-12-21 08:53:34
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 30
Words: 30,616
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21072221
Author URL: https://archiveofourown.org/users/AmeliaSPN1973/pseuds/AmeliaSPN1973
Summary: He was the hottest musical sensation on the planet and you were his new tour manager. You thought he was an asshole. He thought you were a prude. What happens when you spend the next three months with him.





	1. Chapter 1

**Author's Note:**

> Not Beta Read.  
All errors are mine.

Dean Winchester was almost every woman’s fantasy. Winner of every award he had ever been nominated for, there was no stopping him. He was just about to embark on his first World tour and you were just recently assigned as his tour manager by the record label. 

You did your research. His first single blew up the charts, but the video was what won him all the adoring fans. He was absolutely gorgeous; his voice induced orgasms and eargasms around; and he crooned of love, sex, and romance like a member of a boy band. _ This is going to be fun… not. _

You arrived at Staples Center at 3:30 in the afternoon. You were wearing a nice low cut blouse and a knee-length, fitted jean skirt. After his show that night, you would be riding with him in his tour bus to Chicago, onto New York, then flying with him for his European leg of the tour. You were leaving your family and friends for three months. 

Sam, his brother and manager met you at the front gate after you obtained your credentials. 

“Hey Y/N. It’s good to finally put a face to a voice.” 

“Nice to meet you Sam.” You smiled and shook hands as he looked at you and smiled. He was attractive, much like his brother. He was about six foot five with long dark brown hair. He looked like he could give Fabio a run for his money as a Harlequin Romance cover model. 

“So, you know what you’re getting into, I hope?”

You laughed. “I have done my research.” 

Dean liked his drink, likes getting what he wants, and is a womanizer. 

“I’ll be with you guys, because I know my brother. He will make a pass on anything with a vagina.”

“That’s refreshing.” You rolled your eyes. You made it through undergrad and law school to be working for a man who will probably undress you with his eyes and only wants to see women naked in his bed. 

Sam laughed nervously. “Well. Let’s go meet him.”

You followed Sam through the arena, showing your VIP credentials heading backstage, then followed him through another long maze of halls until you get to four huge burly security men. “You’re not not allowed back here.” 

You stood back while Sam walked up to the men. “I’m Sam Winchester, Mr. Winchester’s manager.”

“We were given specific instructions not to let anyone back here.” 

“I was the one that gave those instructions.” Sam provided his credentials and the security detail let him walk back. “Come on Y/N.”

As you passed you heard one of the security guards started talking to the others. “She’s got a nice rack, but she seems too uptight for Mr. Winchester.”

One of the other guards responded. “I don’t know guys. I give her a half hour before she’s down on her knees sucking him off or bent over a counter taking it up the ass.” 

You turned around and glared at them, then continued walking.

Sam stood at the door and began to knock. “Hey Dean. It’s Sam. Are you decent?”

“Come in.”

Sam opened the door and you followed him into the dressing room. From a corner, he walks out in nothing but a towel and a smile… Dean Winchester. 

You glanced quickly first noticing his face, perfectly symmetrical with long beautiful eyelashes, eyes as green as the Lord Of The Rings shire, plump kissable lips, brown hair with flecks of gold, and his body blessed in freckles that do not distract, but enhance his beauty. You looked away quickly but not short enough to notice he was built but not ripped; he had strong shoulders, biceps, pecs, and back. He wasn’t ripped with six pack abs; in fact, his stomach was a bit pudgy, but he was still absolutely beautiful. Your eyes then darted down where his treasure trail began but was blocked by the towel wrapped around his waist. You began to feel your arousal soaking your panties and realized you were physically attracted to him. _ Who wouldn’t be? He’s fucking gorgeous. However, he’s your client. You can’t sleep with him. _

“Like what you see sweetheart?” He turns and winks at you. 

You scoff and look away, yet the blush on your face said otherwise. “I’ve seen better.”

He then began eyeing you up. You were in skinny blue jean skirt, high heels that accentuated your calves, hips and ass and made your legs look longer. You were wearing a thin cold shoulder low cut black blouse that accentuated your cleavage. He didn’t try to pretend he wasn’t looking like you did. He stared at your cleavage, licking his bottom lip and blew a sigh/low whistle as he continued to stare. You see him shift where he’s standing; he was visibly aroused by you. 

You looked at him smugly. “Like what you see?” 

“Actually…” He smirked. “I wouldn’t mind looking further.”

Your cheeks flushed pink as you looked down and away.

“Dean,” Sam looked at his brother. “This is Y/N, your new tour manager. She will be with us during this world tour.” 

Smiling, you got up, walked to him and stuck out your hand. As he shook your hand, his towel came undone and fell off him. You tried to turn your head away fast enough, but you caught enough. His legs and thighs were thick; he was bow legged; and when you saw his package, you knew why. He was slightly above average length, but his girth was definitely above average, and for a penis, it matched him, extremely attractive. 

He didn’t flinch in embarrassment. “Well, I’m putting it all out in the open. Get used to it.”

You were pissed, turned to Sam and grabbed his arm taking him and leading him out of the room. As soon as the door was shut you began talking quickly and angrily. “I’m sorry but I can’t work like this.”

“I know. I’m sorry Y/N.”

“You need to find another tour manager.”

Sam implored with you. “Please don’t. We need someone to help manage his tour. I’ll try to wrangle him in. OK.”

“This is borderline sexual harassment, Sam.”

“I know. I’ll have a talk with him. Just wait out here for a bit.”

He walked back in as you leaned against the wall near the door, breathing and getting yourself together. _ He’s beautiful, but also super cocky. _

You could hear the security guards talking.

“Waiting in line for the next groupie to leave.”

“I’d like to bend her over and tap that ass.”

You glance their way with the evil eye again and they shut up. 

The door then opened behind you and three men walked out. You recognized them as Chuck Shurley, Heavenly Records label president, Fergus “Crowley” McLeod in A&R and Jimmy “Castiel” Novak as head of security for Mr Winchester.

Chuck recognized you. “Hi Y/N. Glad to see you’re taking over as tour manager.”

You stood up and shook his hand. “Yes Sir, Mr. Shurley.”

“Call Me Chuck.”

You looked at him nervously. “OK. Chuck.”

Chuck looked at the men and then you as he spoke. “Crowley and Castiel, this is Y/N. She’s Dean’s new tour manager for the world tour. I think she could be a huge inspiration for Dean.”

You shook each of the gentlemen’s hands. “Hello Darling,” Crowley spoke.

“Hello Y/N,” Castiel said moving close to you. You took a step back and he tilted his head to the side to observe your movements and then took a step back. He seemed to invade personal space.

“Don’t let us down,” Chuck looked at you. 

“I won’t Chuck.”

“Good. Good.” Chuck said as they headed down the hall. 

Sam got you shortly after and you went back in the room and sat down. 

Dean came out of the bathroom in jeans and a thin, fitted t-shirt that accentuated his muscles and his perky nipples. While you already saw Dean naked, the shirt did not detract from his attractiveness. In fact, it left a little more to the imagination. 

“Better sweetheart?”

“Yes. Thank you.” Your mouth was still dry because you could still remember everything you saw earlier.

Sam looked at you. “Can I get you a drink Y/N?”

“Water is fine. Thanks.”

You downed that bottled water as soon as he handed it to you. You got up and looked at the things provided backstage, making sure all items that were included in his backstage rider had been met. 

Sam saw what you were doing and smiled. 

You sat back down after you saw what was there.

“So, you’re coming on tour with me?” Dean came and sat across from you in a chair.

“Yes. I will be overseeing you get to the venue on time, scheduling interviews, meet and greets, radio promos, everything…”

“Everything?” He smirked.

“Everything regarding your needs to be able to put on a great show.”

He tilted his head and looked as you with the same smirk. “I have a lot of needs to fulfill to ensure I put on a great show.”

You swallowed. _ What am I getting myself into? _

He was a cocky one for sure. 

“Well, I’m sure you can get THOSE needs filled without me.” You looked at him smuggly. 

“What if I want you to fill them?” He smiled and you felt your arousal soaking your panties. _ Why is he affecting me so? He’s so cocky but damn, he is beautiful. _You blushed, swallowed, and composed yourself. “I am here for a job. I don’t mix business with pleasure.”

“Well I do,” he said leaned towards you, shifting in his seat and you could see he was getting aroused too.

You sat and stared at each other awhile in silence. 

After awhile, Dean got up heading to soundcheck. You followed Sam to the stage where you sat in the arena and watched Dean play a few refrains on the piano. He was classically trained with beautiful, long fingers that graced over the keys, and you thought what those long fingers could do to you and your arousal began to soak your panties again. He then stood up and played some riffs on guitar. He was talented in the way he could strum that guitar, your panties got wetter thinking of what he could do to your entrance and clit. Then his band arrived and he practiced a few songs with them. His voice was like melting butter.

After soundcheck, you went and got some food with Sam while Dean got ready for the show, then followed Sam to the side of the stage to watch the show. 

Dean took the stage in jeans, a t-shirt and plaid shirt. Even though he was dressed rather informal, like a hunter, he still looked extremely attractive and he commanded the audience. His voice was pure sex. He made sure and held the hands of every person in that front row at some point during that show. His lyrics were oversexualized along with the way his hips would sway. At one point, he came over and sang your way, making eye contact with you, and his words seemed like a promise. “You’ll be screaming my name, our bodies entwined, you’ll be putty in my hands all through the night.” _ Damn! That was hot. _People called his lyrics “panty dropping” and you now understood why. He had you aroused. 

After the show, Sam ushered you to the bus while Dean had his “backstage parties.” _ Probably groupie orgies. _

“He’s getting laid, isn’t he Sam?”

“I stopped asking what he was doing a long time ago Y/N. Why? Could you be jealous?” Sam looked at you quizzically. 

“No. He can fuck any groupie skank he wants.” _ Well that came off as jealous. _

Sam looked at you. “Tell me how you really feel?”

“He’s a grown man. If he wants to have sex with multiple women in one night, it’s up to him.” You had to admit that secretly you wanted to be one of those women, but not in a group. If you were going to sleep with him, it would be with just you two alone.

The bus was going to be crowded. Sam, Dean, Castiel, and you would be sharing the bus. There was a queen size bed in the back, supposedly Dean’s bed. Then there were four bunk beds. You were given one side completely, while Sam and Castiel shared the other side. You went to the bathroom, putting on a sleep shirt and shorts, and went to your bunk. You had a TV, On demand movies, your laptop and iPhone dock, and your headphones to plug in to have privacy. 

An hour later, you heard Dean enter the bus. You were watching a movie, but instead of Dean going to his bed in the back, he jumped in the bunk above you. A few minutes later, you heard tapping on the side of your curtain. “Yeah.” You opened the curtain to see him upside down looking at you smiling.

“Hey.”

“Hi,” you said trepidatiously. 

“Whatcha doing?”

“Just watching a movie.” 

“I’m still a little wound up from the show. Wanna have a drink with me?” He smiled innocently. 

You looked at him and pondered the thought. _ I guess a drink won’t kill me. I won’t end up in bed with him. _

“OK.” He climbed out of his bunk first and then you out of yours, throwing on a robe and followed him into the front couches and little kitchen. Sitting at the table, he got two whiskey glasses and a bottle of Johnny Walker black and set it on the table. After pouring you and he a glass, he lifted his. “To a mutually beneficial relationship.”

You looked at him cynically, but raised your glass then clinked yours with his.

“Did you like the show?” He looked like a kid who was in a play asking excitingly if his parents enjoyed it. 

“It was very eye opening.” You swallowed your drink quickly thinking of the way he made love to the crowd and to you when he sang to you. You had no doubt he probably had a few groupies after the show. 

“It was?” He cocked his head and smirked.

“You have a really unique stage presence. The way you handle the crowd.” You were in awe. 

“I’m glad you enjoyed yourself.” He smiled and you shifted, feeling your arousal pool again. “I hope to give you a one on one show sometime.” He smiled and you were completely turned on by what he just said.

He began to lick his bottom lip and you look down realizing your robe had opened and your too thin sleep shirt was revealing your bare breasts. You closed your robe quickly and downed the rest of your drink. “I really must be going to bed. We can talk more in the morning to get Sam and Castiel’s opinions on this tour.”

He smiled and swallowed his drink pouring him another. “Sure. Good night Y/N. Sweet dreams.”

“Good night Mr. Winchester. You too.”

“Call me Dean. I insist.”

“Good night Dean.”

“I won’t have as good of a night without you,” He licked his bottom lip again and smirked. 

When you turned away from him, you began to smile realizing he was attracted to you. _ He’s such a player. _ Something in your heart felt different though. _ Men can change. _

You crawled into your bunk, closing your heavy curtain, locking it, and sighing loudly. It provided protection from people getting in, but at this moment, you were thankful it wasn’t going to let you out easily. 

You heard him crawl above you and you breathed heavily. You fell asleep with a phantom feeling of his weight against you. 

That night you had an erotic dream about him. 

_ His plump lips were against yours as he kissed with a passion setting a fire in your belly. “I’ve been wanting to do this with you so long Y/N.” His lips moved from your mouth down your neck and settled into the crease of your neck, where he nipped and sucked leaving marks. _

_ “Please Dean,” was all you could say as you wrapped your arms around his neck. _

_ He peppered your chest in kisses as he lowered the straps of your bra and unclasped your front clasp watching your breasts fall out. “Beautiful.” _

_ You felt the heat of his breath as he puckered over a nipple and sucked it in until it was hard. _

_ “Fuck.” _

_ “Fuck’s right. God! You are so beautiful,” he said as he paid attention to your other breast next. _

_ Slowly his lips moved down your torso as you squirmed underneath him in pleasure. He took his time kissing your inner thighs as your arousal began to slick down your legs. You felt him lick your slit and next thing you knew he was eating you out as you moaned and writhed against him. _

_ You felt his tongue enter you, over and over as his thumb strummed your clit and you cried out. He then switched things up letting one, then two of his long fingers enter you, curling up and hitting your g-spot as he sucked on your clit. You came hard, your legs shaking, as he kissed up to your mouth and you tasted yourself on his tongue. He then slotted between your legs as he entered you and he let you adjust. _

_ “Yes,” you cried out as you moved together, back and forth, rocking in that tiny bed until you finally felt your second orgasm and grabbed him tight. _

_ “Y/N. I love you,” he said as he spilled deep into you. _

_ “I love you too Dean.” His lips met yours and he kissed you until you could barely breathe. _

You awoke abruptly, breathless, sweating, and shaking. _ Shit! _

Above you, you heard his grunts. “Fuck Y/N. Take it Baby. Take it. Yeah! Fuck! You feel so good!”

You turned a bright shade of red as you rolled over to your side and put on your sleep mask with headphones, putting on your sound machine to drown out his grunts and moans. You weren’t sure if you were moaning in your sleep as well or if he was just getting off with you asleep underneath him, so you didn’t say anything. 


	2. Chapter 2

The next week included stops in Chicago and New York with your nights spent in the bus. You were learning to get along, get to know Dean, and to not take him too seriously. Unfortunately, you had to witness his morning erections and more nightly grunts and groans, while that back bedroom stayed empty. 

You almost asked if you could stay in that back bedroom to distance yourself from him, but didn’t know what that would “cost” you. Not that you didn’t mind. He was making you sexually frustrated hearing him speak your name at night, which caused you erotic dreams about him. You didn’t tell him what you heard and he didn’t say anything to you; however, both Sam and Castiel were both keeping tight lipped around you two, so it made you believed they could both hear each of you sleep moaning, which embarrassed you. 

During the day, you discussed your tour ideas and made sure Dean got to where he needed on time. Dean basically gave you full authority to work it all out with Sam and Cas while he spent his free time writing songs, meeting groupies, or playing video games. 

In the evenings, you stayed up way too late talking to Dean about everything not work related and having a few drinks. Despite his womanizing ways, he could be quite the gentleman. You seemed to share things in common and he made you laugh. He was funny and sarcastic, when he wasn’t trying to get laid. 

After the two nights sold out Madison Square Garden shows, the last night in New York, before  _ traveling _ overseas, you got to stay in a five star hotel since the bus was being sent back to the garage he stores his tour bus in. You, Sam, Cas, and Dean went out for a late dinner and then went back to Dean’s penthouse suite with three bedrooms. 

“You take my room Y/N. I don’t really sleep,” Cas offered. 

“You sure?”

“Yeah. I can rest on the couch if needed.”

Cas went down to the lobby to talk to hotel security while you and Dean stayed up talking in the living area. Sam excused himself and went to his room. 

“Are you ready to go to Europe tomorrow?” You looked at Dean curiously.

“Been there. Done that. I bet you are though.”

You smiled. “I am. I always wanted to go to Europe, so this should be nice. The views should be beautiful.”

“I’ve seen better,” Dean said looking at you and you swallowed, blushed, and looked down in embarrassment.

Dean moved closer. “I’ve waited this whole week to ask, but may I kiss you?”

You looked up and into his olive green eyes. “OK.” You were trepidatious. 

He moved in slowly, placing his hands on your cheeks. His lips pressed to yours and you felt his plump lips. The kiss was tender but began to get needy as you moved your lips with his. He began to wrap his arms around you and you did the same as you began to explore each other from the outside of your clothes. Dean moved his leg between yours and you immediately began to grind against his strong thigh.

”Fuck. I want you,” he said between kisses as he held you closer and slipped his hand up your shirt finding a breast to knead. 

“Fuck. Yes.” You moaned wanting to get closer to him. You began to palm the bulge in his pants, his boner prevalent through his jeans.

“Fuck,” He grunted. He finally grabbed you up in his arms, your arms around his neck, and legs wrapped around his waist, as he held you by your buttocks and carried you to his room. 

Opulence at its finest, he laid you in bed across the gold threaded duvet, pulled away to take off his flannel shirt and climbed onto the bed hovering over you. “Man. I have wanted you all week.”

“Me too,” you confessed nervously. 

You began undressing each other slowly never pegging him as a romantic, but he surprised you. You liked the surprise.

Once you were down to your black laced panties and boxer briefs for him, he smiled. “You are so beautiful.” 

You smiled nervously. 

He began kissing down your neck, peppering your chest with kisses as his lips puckered over your nipple. 

You moaned loudly as he continued with the other side.

Moving down your abdomen, he kissed down between your inner thighs and took his time as your arousal soaked through your panties slicking down your legs. Moving your panties to the side, he made a long lick up your slit. 

“Fuck,” you moaned. 

Continuing to lick, you writhed against him. 

“Fuck! You taste amazing Y/N.” 

“Oh God.”

He was sucking on your clit, his finger pumping your entrance, getting you closer to orgasm as you reached down carding his hair. 

“Oh Fuck. I’m so close.” You we’re starting to clench around him, so he applied the pressure you needed and you came hard. He worked you through your orgasm, then moved up to your mouth to kiss you passionately. 

You kissed for a while feeling each other and tasting yourself on his tongue. He was definitely more romantic than you ever thought he would be. “I could have stayed there awhile. You taste divine,” he said smiling. 

He took a moment to pull off your panties, then took off his boxers. Smiling, he looked down into your eyes. He interlocked his fingers with yours and pushed into you slowly working his way inch by inch until he bottomed out giving you time to adjust.

You began your match; his thrusts to your bucks, hitting your g-spot, making you cry out each time. 

“Damn. You’re so fucking tight sweetheart. So good.”

“Oh fuck. You are so big Dean,” you moaned as he continued. Your walls fluttered around his thickness with each drag of his cock.

“Please Dean.”

“Please what?”

“Harder Dean.” You wrapped your legs around his waist to change the angle. 

Thrusting harder, you were getting close. You scratched down his back with your nails as he leaned in and puckered his lips over one breast then another. 

He reached his hand down between your bodies to rub your clit, giving you the pressure you needed to come first. He then picked up the pace to fuck you hard and fast until he had his release, as you dug your nails into his biceps. “Damn! You feel so good Y/N.” He came with a grunt, filling you. 

He leaned in and kissed you tenderly, then rolled to his back, and you rolled to yours. “That was awesome,” he smiled and sighed.

All you could muster was, “Wow!” He was amazing and you felt something with him more than just sex, but as you looked at the ceiling, you realized what had just happened. “Oh My God! What did we just do?” 

“What’s wrong sweetheart,” Dean said on the cusp of slumber. 

You sat up, covering your breasts with your arm, and moving the sheet up over your waist. “Oh God! I’m so sorry Dean. This was a big mistake.”

“What?” Dean sat up and looked at you.

“We barely know each other. I’m not this type of girl that fucks some guy after only knowing him less than a week, regardless of who he is or how good it felt.” You got up grabbing your underwear; turning your back to Dean, slipping them on; and began searching for the rest of your clothes. 

“You can stay in here with me tonight if you want.” He smiled and patted the bed next to him.

Finding the rest of your clothes, you slipped on your shirt, pulling down the ends to cover your ass and headed towards the door. “I can’t.”

“Y/N? What’s wrong?”

“I can’t do this. I can’t do this with you right now Dean. This was a total mistake. It was… amazing, but I have a job to do with you the rest of this tour and I can’t get involved. I’m sorry. I didn’t mean to do this. Let’s just go back to before tonight, please.”

“But maybe I don’t want to Y/N.” Dean smiled. 

“I just can’t Dean.” You left his room shutting his door, running to yours and locking it. You took a deep breath as you leaned against the inside of your door. You were still feeling the aftershocks of your orgasm. You didn’t know why you needed to leave.  _ He wanted you. You wanted him. You had amazing sex. Why didn’t you stay the night?  _

You couldn’t understand why you didn’t. Then you thought about all the women he probably slept with that week alone and was nauseated as you realized why.  _ I’m just another groupie but I don’t want to share him with anyone else.  _

Dean rolled to his back and breathed.  _ Why did she just leave?  _ His erection was coming back; he was angry and confused. He wanted you; he wanted to be inside you again; he wanted to just feel you against him. He missed the connection and you felt like someone he wanted to actually sleep in the same bed with, not just sex. He hadn’t been rejected in a long time. Then he thought about his conquests over the last week and realized with all the women he’d slept with, you probably thought he was just player. He made a pact with himself.  _ I won’t sleep with any other women in Europe to make her see I want her.  _

He grabbed his pillow, smelling you on it as he grabbed and stroked himself until he released again thinking of you. 

You laid down in your bed. The ache between your legs felt good; he felt good. You wanted to feel him inside you again. You wanted to lay your head against his chest and feel something, maybe even loved or wanted. You hadn’t been in a relationship or had sex in two long years, and he felt so good, but you figured he probably was a player and would have kicked you out shortly after fucking you anyway.  _ He probably doesn’t even cuddle.  _ You realized you probably left in the right amount of time, rolled over to your stomach, closing your eyes, and tried to go to sleep. 


	3. Chapter 3

You entered the cabin of the private plane and sighed. In one row, Sam and Cas sat. Another row, Chuck and Crowley sat. The only row left was the row Dean sat in. 

You took your seat next to him. Before Dean could even say anything to you, you put on your sleep mask with headphones, rested your head against your neck pillow and closed your eyes. You weren’t ready to talk to Dean yet.

Dean looked at you wanting to talk about what happened the night before, but you cut him off. 

Seven hours later, you landed in London. You sat between Crowley and Chuck in the limo to the hotel, still keeping a distance from Dean. When you got to the hotel Chuck and Crowley ushered you into an elevator, making Dean, Sam, and Cas take another. 

Chuck looked over at you. “We’re going back to America tomorrow Y/N, so I want to make sure you are ready to do this?”

“Of course Mr. Shurley… I mean Chuck.”

He looked over at you with concern. “It just seems that you and Dean are not getting along. You didn’t talk the entire flight and it looked like you wouldn’t even speak to him.”

You put on a smile. “We were testing out our boundaries this week. I think we have clearly marked the line that we shouldn’t cross now.” You had already crossed the line, but Chuck didn’t need to know that. You have now put down the line that you promise you will never cross again during the tour.

“Darling, I wouldn’t draw any lines in permanent marker if I were you,” Crowley smiled at you.

You looked at both men and spoke confidently. “For this tour, clear lines have now been made. Will the lines ever get crossed, I don’t know, but right now, my job is to be a tour manager only.”

“Fair enough,” Crowley looked over at Chuck. 

“Just think about what Crowley said Y/N. I chose you for a reason. I think you will inspire Dean in more ways than one.”

“OK,” you said confused as the elevator stopped on your floor and you stepped off. 

“Good luck Y/N,” Chuck said smiling. Crowley smiled too. 

“Thank you gentlemen.” The door shut and you headed to your new room in the suite. 

When you entered the room Sam and Cas were nowhere to be found but Dean was sitting on the sofa. “Hey Y/N.”

You smiled and started to walk past him. You didn’t want him to know you didn’t want to be around him because you were afraid you would sleep with him again. “Hey Dean,” you said absentmindedly.

“Are we going to talk about the elephant in the room?”

“What?” You turned and looked at him. 

“The fact that we slept together and now you don’t want to be near me.”

You smiled at Dean walked over and sat down. You tried to calm your heart that was beating like a jackhammer. “I can be near you.”

“Y/N. Your heart is beating as wildly as mine. I don’t see what’s wrong with what we did. In fact, I think we should try this again.” He reaches out and gently put his hand on your knee.

You immediately brushed it off. “Dean. I can’t. It goes against all the rules I have made for myself in this business I am in.”

You saw his eyes; he seemed hurt by your rejection. He looked at the time. “Can we at least go and have some dinner? It’s early and I know with jet lag, you don’t want to sleep now, and I really can’t go out alone due to the risk of being mobbed, shot, or abducted.”

“OK.”

You walked down the street to a little pub in London to eat and listen to some live music. When the English band playing noticed Dean in the pub, they asked if he would join them on stage to play some of his songs. He obliged and went on stage singing three of his hits. After singing with them, he was no longer left alone. He spent time at your table signing things and taking selfies with everyone in the pub. You became the photographer for all the groupies who were trying to vie for Dean’s attention. One girl got up the nerve to look at you and say, “be a doll and fetch me an appletini, and what about you Dean?”

However, Dean immediately made them aware that you were his date and you were not just someone they could push out of the way. “Thanks, but as you can see my lovely lady and I are enjoying some time checking out London before my show tomorrow night. I hope you can see the show tomorrow.” He moved closer to you, wrapping his arm around you. You weren’t sure if he was just avoiding this woman or if he genuinely wanted to be near you. You smiled genuinely, moving into him as you wrapped your arms around his torso. Smiling, he kissed your temple, and you were starting to get the same feelings you had before sleeping with him the prior night. 

You walked back to the hotel with his arm around you. When you got back to the suite, Dean walked you in and to your room. “Thanks for coming with me tonight. I had a good time.”

“Me too,” you said smiling. “Thanks Dean for making me feel important.”

“You are important. I know you don’t want to have sex with me right now, but I do hope we can still be friends.” 

“Sure Dean. I‘d like to remain friends.”

He leaned in and hugged you. “Good night Y/N.” You felt his arms around you as you both held each other longer than you should have. You finally pulled way as you stared into each other’s eyes, pining. He finally smiled and winked as he walked towards his room. 


	4. Chapter 4

The next six weeks were crazy and you were on your manager duty the entire time. During the day, you made sure Dean met all his appearances, interviews, meet and greets, and showtimes. After the show, you and Dean took things slow, spending most nights up way too late talking on the train from England to France, to Amsterdam, then Germany, and onto Italy. Sometimes Sam and Cas would go to the food or bar car, letting you two alone in your sleeper car where you enjoyed making out with Dean and feeling each other up on those long rides. He was quite the romantic, even though there was no sex during that time. 

When you finally reached Venice, it was an extremely busy day. Dean had five interviews throughout the day and you made sure he met each one in time. You then got him back to the venue in time to do his soundcheck and have a few hours to get in the zone. 

As you watched him go through his pre show rituals, you felt almost like a proud girlfriend, yet you weren’t. _ Are we something? _

Dean did his show and again wooed another crowd of horny women including you with his voice and his hips. He left the venue with you immediately after, not having an after party or his share of groupies. He had not had after parties or groupies since New York. 

You traveled back to your hotel by gondola. You were chilly so he took off his plaid flannel shirt and covered your bare shoulders and arms. He then wrapped his arm around you as you looked at the lights at night. He finally leaned and kissed you tenderly, the fire in your belly beginning. When you returned to the hotel room, you crashed onto the couch with some wine and turned on the TV to unwind. Your feet were killing you from standing all day.

“Here. Let me.” Dean tapped his thighs.

“OK.” You put your feet up on his lap. 

He slipped off your shoes and gave you a foot massage.

“Wow.” You moaned at the way he was making your feet feel.

“You like this?”

“Mmm hmm.” Your eyes were closed as you relished in the feeling. He then began to massaging your ankles up to your calves which also felt amazing.

You weren’t thinking as his hands slowly massaged up your legs as you leaned your head back, eyes closed. You instinctively began to spread your legs as he got closer to your inner thighs. 

Dean then began placing gentle kisses up your leg. “Do you want this Y/N? Do you want me to continue?”

“Mmm Hmm.” You moaned as he inched up your skirt. Your breath was getting shallow as your arousal began to pool. You were wearing thigh high pantyhose and a lacy black thong underneath your skirt. When his lips reached inner thighs, you opened your eyes to see him between your legs. 

He stopped and looked up at you. “Do you want this?”

You stared at him, your panties soaked. It had been a month since you first slept with him. He had been nothing but a sweet and caring boyfriend that last eight weeks You realized you did care for him and wanted all of him. This was your moment to back down, but you couldn’t. “Please don’t stop.”

He smiled and dipped down between your legs kissing between sides. “Oh Fuck Y/N. You do my know how long I’ve wanted to do this to you.” He kept it up as you writhed against him. 

He looked at you for permission and you nodded, letting him slowly pull down your panties. When he returned, he slowly licked from your entrance to your clit and you moaned loudly. The feeling he was giving you was pure ecstasy. Before long, he was eating you out with fervor as you moaned and writhed against him. He tongue fucked your entrance, while his thumb rubbed your clit, getting you closer to bliss. He then switched and began with pumping your entrance with one then two fingers as sucked on your clit. You came hard against his face and he moved up and kissed you. 

Rolling him over, you took your turn. You undid his jeans, pulling them down along with his boxers and went to work on him, kissing and licking down his chest and torso. He leaned on his elbows and watched at you as you took your time and licked the main vein underneath, taking the tip of him in your mouth. He was average length but he made up in girth. “Fuck Y/N.”

You continued swirling your tongue around the tip, then brought him fully in your mouth to the back of your throat. “Shit!”

You looked up at him with lidded eyes as you sucked, wrapping your one hand around the extra length while the other squeezed his balls. 

Grabbing your head, he began to thrust into your mouth over and over. “Oh Fuck Yes! Fuck! I’m gonna cum Y/N.” You kept going as he came hard in your mouth shooting out strands of cum. You took what you could, some coming out the sides of your mouth, continuing to swallow, then licked up around him. 

“Damn! That was the best blow job I’ve had in so long Y/N.”

You kissed up his body as your lips met tasting each other on your tongues. 

“I want so bad,” Dean professed.

“Me too.” You gave up trying to pretend you didn’t want him. You did. 

“Ride me sweetheart.” 

You looked at him and then looked around, getting shy. “Shouldn’t we take this back to your room. What if Cas and Sam comes back?”

“They won’t be back for awhile. I’ll make this the ride of your life Baby.” Dean continued to look at you smiling. You straddled his waist and aligned his cock to your entrance as you lowered yourself letting him impale you. “Fuck,” you moaned as he filled you, fitting perfectly in you. 

You began undulate your hips, starting at a slower pace. Before too long your were bouncing on his cock, riding him hard, as he reached his hands up your shirt and kneaded your breasts. “Yes Dean.” You peeled your shirt off and undid your bra letting Dean sit up and pucker his lips over your nipple, to suck it hard. 

“Fuck Y/N. Your tits are fucking great.”

You were both too close to orgasm, moaning so loudly that you didn’t hear the door open to Sam and Cas. 

Your back was to Sam, who just laughed thinking Dean was with a groupie. “Sorry Dean,”

Sam said.

Neither of your heard them. Instead, you cried out as your orgasm hit. “Fuck! Yes Dean! Yes! Yes!”

“Fuck! I’m right here too sweetheart.” Dean held onto your hips tight as he pumped three times and came with a loud grunt. You leaned down and kissed him passionately as Dean wrapped his arms around you, running his hands up and down your back. 

“Y/N?” Sam quietly said as he looked over at Castiel. 

“I think it is. Let them have their privacy,” Castiel said as they walked to their separate rooms. 

“Yeah. They deserve it. This should raise some interesting questions tomorrow,” Sam mumbled as he headed to his room. 


	5. Chapter 5

You awoke in Dean’s bed tangled up with him in a pretzel of limbs. You remembered him carrying you back to his room where you had three more rounds that night, finally collapsing in his arms after four in the morning. It was his day off, so you had slept in until nine. 

You worked your way out from under the tangle of Dean and got up, wrapping a sheet around you and began looking for your clothes, realizing they were strewn over the living area after having sex with Dean on the sofa. 

“Where you going?” Dean began talking to you but his eyes were still closed. 

“Uhh...Bathroom.” You were trying to sneak out to your room, but he caught you. 

“When you get done, come on back to bed babe.” He flipped over to his stomach. 

“OK,” you said to deaf ears as he was snoring again. 

You did your business and walked back into the room. You quickly removed the sheet and hopped under the covers. Eyes still closed, Dean turns to his side as he reaches his arm out putting it around your waist and pulling you to him. As soon as you were close enough to feel his breath on you, he nuzzled into your neck and spoke quietly. “Damn Babe. You’re the best sleep I’ve gotten in years.”

You smiled. “I slept pretty good too.” He moved in closer as his lips began lazily kissing your neck. “Mmmm. I torn between sleeping some more or fucking you.”

You chuckled. You were undecided as well. You could sleep in his arms or scream his name as he pounds into you. Letting him make the decision you responded with, “whatever you decide.”

His lips continued lazily pressing against your neck and then slowly down your body. Next thing you knew, Dean was eating you out. “Fuck you taste good in the morning. I still taste me in you.“ Dean’s head lowered back between your legs and let his tongue dip back into you, causing you to moan. After an intense orgasm, he crawled back up and slotted between your legs for some amazing morning sex. 

You got up, wrapping a sheet around you and padding quietly to the shower. You turned on the water to warm up and looked in the mirror. Your face was glowing. You smiled. You had an amazing night and morning with Dean. You stepped into the shower letting the water pelt down on your skin. You stuck your head under the water thinking of Dean’s touch when you felt hands moving around your waist and lips next to your ear. “Hey Beautiful.”

“Hey.” You smiled feel his lips begin to tenderly kiss your neck. He slowly turns you around leans in and kisses you. You wrap your arms around his neck and card his hair. 

Reaching down, he hooked his arms underneath your thighs, hoisting you up, holding your buttocks while you wrapped your legs around his waist. 

You kissed him passionately as he lowered you on his cock, impaling you. “Fuck!” 

“Damn! You are so warm and tight baby.”

You ground your hips; his hands squeezed your buttocks as both your grunts and groans increased. “Yes Dean. You feel so good.”

Dean kissed down your neck, across your shoulder and down until he puckered his lips over your nipple, grazing his teeth over the hardened pebble, causing you to moan.

He then switched sides as the water rained down on you both. 

You both were getting so close. You ground your hips harder as he reached between your bodies, rubbing your clit and you viced around him, causing your orgasm and his as he released in you. 

Lazy kisses and bodies clean, Dean ordered room service for the both of you, and you enjoyed a big waffle, butter, and syrup while sitting up in bed. 

“What do you want to do today?” Dean asked with his mouth full of waffle.

“I’d love to play tourist and look around to see what there is here.”

“Absolutely. This could be fun. I haven’t ever done it before, at least sober, so maybe I will see what’s here. Castiel will have to come for security of course, but we can go wherever you want babe.”

You smiled. “Sam can come too if he wants.”

“Sure. The more the merrier.” You could hear his sarcasm.

Sam didn’t go, deciding to go sightseeing by himself.

Dean held your hand as you spent the day sightseeing as Castiel kept a watchful eye. Fans would approach Dean for pictures and you didn’t mind taking the photos with their phones because Dean made sure to let them know you were his woman with a soft hand to your back, a smile, a wink, and even a few PDA kisses. A few of the groupies who had seen Dean before and were accustomed to his affections only knew you as the new tour manager, so they tried to ask Dean out. However, Dean would smile and explained that he was out with you, grabbing your hand and showing them he was being a committed boyfriend. The catty eye rolls and snickers as they talked behind your back was unnerving until Dean grabbed you close, dipped you and kissed you passionately in front of them. 

You both pulled away when you both could no longer breathe and the groupies left. 

That night in bed, you decided to see where Dean’s thoughts were on your relationship. “So Dean. Just wondering what you think this is.”

“What is sweetheart?”

“This. Us. Sleeping together. Sharing a bedroom. Sightseeing together. I am just curious what you would call us.”

Dean turned to his side and smiled his thousand watt smile at you. “Whatever you want us to be Y/N. I don’t want to put a label us or anything, but I’m having a good time with you and you seem to be having a good time with me, so, let’s just keep having fun together until we need to talk more about this.”

“OK.” 

He pulled you close to him and his lips began peppering your neck in kisses. “Right now, let’s have some fun,” he said as his began kissing down your body. 


	6. Chapter 6

You were traveling from Italy to Australia by private jet with a flight time of eighteen hours. Sam and Castiel sat in the front row of seats while you and Dean sat in the back row; a blanket covered you both as you kissed, your seats reclined back, and your hands ran up and down each other’s bodies. 

Your breath hitched as his thumb and finger tweaked a nipple, and he groaned when you palmed his bulge. 

His hand slipped up the hem of your skirt, up your thigh, the blanket covering your immodesty. He grabbed your ass and moaned. “Oh Fuck Y/N. You’re not wearing panties.”

“I guess I forgot,” you said with a smirk and bit your lower lip. 

His fingers moved to your inner thighs. “Fuck Y/N. I want to fuck you so bad.”

“I’m not a mile high club member yet.” 

Dean cocked his head, looking shocked at your confession. “No?”

“No.”

He smirked. “Well then, we have a long flight and plenty of time. I’m going to personally induct you into the Mile High Club and make sure you’re a solid member.”

You smiled. 

He begins to dip a finger into you as his thumb massaged your clit causing your breath to hitch. 

He placed one of his hands behind your head pressing you to him, kissing you passionately, devouring your moans as he thrusted in and out of your now wet entrance. Barely giving you time to breathe between kisses, he added another finger to scissor into you.

“Oh fuck,” you moaned between breaths. He captured your mouth again, moving faster. Your moans got louder so he sucked on your tongue to stifle your noises.

You finally clenched around his fingers; vision going white as your orgasm washed over you. Dean continued to work you through your orgasm, removing his fingers, pulling away from the kiss, bringing his fingers slick out in your arousal to his mouth and sucked them clean. “Oh how amazing you taste, baby.”

You whispered to Dean. “Oh God Dean. That was amazing.”

Dean smiled. “Oh Baby. I’m not done by a long shot. This was just foreplay. Go to the bathroom and I’ll meet you there shortly.”

You go to get up but your legs are still a bit wobbly from the strong orgasm you just had. “You OK Y/N?” Dean was chuckling as he said it. 

Cas and Sam turned around. 

“I’m fine. Just a leg cramp. Give me a minute.”

Dean smirked. “Those can be a bitch.” He then lowered his voice “Wait till I get through with you.” 

You gushed with arousal at the thought which promptly made you stand, grab your purse and announce, “going to the restroom.”

“OK Sugar.” Dean chuckled.

You got into the tiny bathroom wondering how you and Dean were both going to fit. You weren’t a petite woman. You splashed cold water on your face and cleaned yourself with some feminine wipes when you heard a knock. “It’s me,” Dean said quietly.

You unlocked the door and stepped back as he opened and shut the door behind him. He grabbed you, kissing you passionately as he lifted you up and set you on the small counter. His hands first traveled up the inside of your shirt as he raised it up around your neck. He was then able to pull the front of your bra down and capture your nipple with his mouth, sucking it until it was hard. His hands began traveling up the hem of your skirt, along your thighs, as his lips caressed your neck. “Fuck! I need you so bad,” he confesses. You pulled his belt off swiftly then popped the button of his jeans and unzipped them. “Thanks. I needed that.”

“You’re welcome,” you smiled, pulling down his jeans and boxers at the same time. 

“Shit! You’re fast.”

“I need you in me just as bad Dean.” You spread your legs; your skirt was now above your waist; your bare ass on the counter. He moved between your legs, pressing his hard cock against your entrance. Wrapping your legs around his waist, he placed his hands on your hips, looked at you, and in one swift thrust, he was deep seated in you causing you to cry out. 

“Fuck Y/N! You’re so wet.”

“It’s all for you.” You moaned out as you moved your head to capture his lips. 

He began to move and soon you were both moaning and grunting loudly, neither giving a care if Sam and Cas could hear or not. 

With each thrust, he was hitting your g-spot. The small bouts of turbulence jostling the plane made his thrusts change angle causing you to cry out his name. “Fuck Dean! Harder.”

He thrusted harder as his hands played with your breasts. “God! I could stay like this. You feel so fucking good.” 

“Me too, but I’m getting close Dean.”

“Me too.” He stuck his hands between you and began to circle your clit. Before long, your walls caved around him causing his release and you cried out in ecstasy as he groaned. 

He captured your mouth, kissing you passionately. “You’re so fucking good baby.”

“You too.” 

He pulled out, helping you down from the counter and turned you around. He grabbed your hips as he moved up behind you and thrusted into you from behind. “Fuck! You feel good from this angle.”

“Wow Dean.”

He continued taking you from behind until you both cried out in ecstasy. You both cleaned up, then left the restroom and returned to your seats. 

Sam turned around and glared at you both. “You done fucking yet?”

“At the moment,” Dean quipped. 

Sam turned back around as you both sat down and put on your seatbelts. You then snuggled against Dean’s shoulder and fell asleep. 


	7. Chapter 7

You landed in Australia. Your first stop was Adelaide where the tour started off without a hitch. The show was perfect and Dean was amazing. After the show, he grabs you up as you climb into a tour bus along with Sam, and Cas to travel across the country to Brisbane then down the coast. Dean and you took advantage of the large bed in the back of the bus, much to the chagrin of Sam and Cas.

“Fuck Babe. I just can’t get enough of fucking you,” Dean said as he thrusted hard into you as you clenched around him; you’re orgasm washing over you as you felt him release in you. He collapsed on you, peppering your shoulder in kisses, then rolling over to his back as you both came down from your highs. “Move into my LA home when we get back to the US.”

You turned your head and looked at Dean, making sure you heard him right. “Really?”

Dean turned to his side. “Yeah. Really. I thought about what we talked about in Italy and I just don’t think I can just walk away from you, from this, when the tour is over.”

“Wow!” You were shocked. You smiled. “Yes. I’ll move in.”

He pulled you close and kissed you. Rolling to his back, he smiled. “Ride my face baby.”

You straddled his chest and inched your way up his face, lowering yourself over his mouth, nose and chin as he wrapped his arms around your thighs to keep you upright and ate you out with such fervor that you were holding the headboard so hard that you had hand cramps and you cried out Dean’s name so loud that you scared the bus driver.

Brisbane was the next stop, then Gold Coast, then a long trek to Melbourne, Canberra, then up to Newcastle. During this time, you and Dean were fully invested in each other, making plans to move into his house once you came back from tour. When Dean told Sam, Sam was happy for you both. He never expected his brother to settle down, and he never expected you to be that person, since your first meeting with Dean was so volatile. However, when Sam saw you two together, he understood. 

You and Dean were great together. You were the Ying to his yang. You calmed him down, you grounded him. You were happy together, spending his time with you. You weren’t always having sex. Yes, you had a lot of sex with him, but you just enjoyed being in his company. A typical day on the tour was you and Dean lying together in the greenroom on the sofa, curled up, just letting your breathing and heart rates sync together. You were one unit. 

The best part of the tour was since you were living on a bus, you had to shower at every city’s venue. You and Dean always enjoyed a good shower together. In a large communal shower, you were pressed against the wall, Dean held your buttocks in his hands, your arms were around his neck, and legs around his waist as he thrusted into you causing you to cry out his name with each and every thrust. His lips would take turns puckering around each breast as you felt the warm water fall on you two. You’d then spend time washing each other off slowly, which usually ended with you back against the wall again, only your front was pressed to it as he fucked you from behind, massaging your breasts as you clenched around him causing your orgasms.

After a nice shower, Dean would dress and do his radio interviews, then his meet and greets which he seemed not to enjoy so much anymore since he had you. He would then do soundcheck, you two would eat, then hang out in his dressing room until it was time to take the stage. A last kiss and “I love you,” you would let him and his band take the stage as you hung out to the side with Sam and Cas watching like a proud girlfriend. 

After the show, you rushed Dean back to the bus pawing his clothes off in that back bedroom, licking the sweat from his skin; you were so turned on by watching him gyrate his hips and sing his provocative lyrics. Dean enjoyed your amorous side after the show, letting you take charge as you worked him over until he was so exhausted that he fell into a complete and peaceful sleep. 


	8. Chapter 8

Once Dean had his final show in Sydney, he would have an entire week off before heading to Tokyo for the last shows of the tour. You were excited to have time off in Sydney because your best friend lived there and you hadn't seen her in five years.

For that last show, you left the VIP passes and tickets for Belinda at the front desk and gave her your cell phone number to call when she got there. You were in the shower with Dean on your knees, deep throating his cock, his hands on your head while your hands squeezed his taut buttocks, as you sucked him off until he released in your mouth and you swallowed him all down when you heard your phone go off. Dean looked down at you as you released him with a pop and you began to get up. “Where are you going baby?” 

“My friend’s here. I need to get dressed and go meet her.”

Dean grabbed your arm and smiled. “She can wait a bit or Sam can get her. It’s your turn.”

He pulled you close, turning you around and pressing you against the wall. He began kissing your neck, working his way to your nipples where he teased and sucked on the pebbles until swollen. You moaned as he continued kissing down your torso, slowly dropping to his knees as he lifted your leg over his shoulder and began kissing your inner thighs. He then took his time as he ate you out. 

“Jesus Dean!” He was fucking you deep with his tongue as his thumb rub the bundle of nerves. You held onto Dean’s head, riding his mouth as he kept you pressed to the wall. You were overstimulated when you came with a wail yet he continued to lap and suck at your clit until you pushed his mouth away. He looked up with an innocent but mischievous smirk and you had to laugh at how cute he was. “You OK?”

“Too much Dean.” Your legs were shaking. He gently put your leg down but kept you pressed against the wall as he moved up and kissed you lazily until you got your legs back. As soon as you did, you grabbed tour towel, drying yourself, then headed to your clean clothes so you could go and meet your friend. “I’ll be back shortly. I have to get Belinda from will call.”

“OK babe. By the way, I had fun.” Dean smirked as he stood there naked twisting the towel, snapping it as it swat your ass while you were bent over putting on your panties. “Dean!” You rubbed the red mark on your bottom.

“I had to. It was either that or since you were bent over on display for me, it was to fuck that sweet ass of yours.”

“Dean.” Your head was shaking at him and you were rolling your eyes.

He was standing near you in his towel, as you finished dressing. You walked over and pecked his lips. “Be right back.” 

He looked at you and smirked. “I’ll be right here waiting for you.”

“Well Dean, I’m coming back with a guest so unless you want a repeat of the first time we met, please put on some clothes.”

“Only for you sweetheart.” He smirked.

You rolled your eyes and left. You hurried down to the will call and saw your friend sitting. You rushed over to her and hugged her. “Belinda. It’s so good to see you. Sorry I’m late.”

“Me too.” She saw how pink your face was. “You OK Dear?”

“Oh. Just a little warm. I was rushing here.”

You both began walking the arena, down to where you enter for backstage. Belinda looked at you. “I can’t believe you are managing The Dean Winchester.”

“Yeah. I am. I can’t believe it either.” You smiled. “By the way, I’m also dating him,” you said quietly. 

She stopped you. “You’re what?”

“I’m dating him.” Your voice was a whisper.

“For how long?”

“Two months now. We finally made it official in Italy. He’s even asked me to move in with him when we get back to the USA.”

“That’s great news.” Belinda smiled. She knew you always kept love at bay for your work, but now you finally found someone without compromising your job.

“Thanks.” You enter the backstage and headed down the halls to Dean’s dressing room. You stopped by the door. “Let me see if he’s decent before I introduce you, OK?” 

“Sure,” Belinda laughed as she stood outside.

You walked into his dressing room. “Dean? Honey? Are you decent?”

Dean walks out in lounge pants and a hoodie. He still looked incredible being so casual.

“Good. Belinda is right outside. I’ll bring her in.”

“Sure.” He smiled. 

You opened the door and looked at your friend. “Coast is clear. Come on in.”

You and Belinda walked in and up towards Dean. He immediately wrapped his arm around your waist.

Smiling, you looked at your friend. “Belinda. This is Dean Winchester. Dean. This my dear friend Belinda.”

“Nice to meet you,” she said as she shook hands with Dean. 

“Good to meet you. You’ve got a great friend here.” Dean then leaned in and kissed your lips and you sat down. You sat on the sofa long ways while Dean sat between your legs and laid his head back against your chest like he would when you weren’t making out or fucking. You absentmindedly began carding you’re fingers through his hair and he loved it, while Belinda sat in a chair across from you. 

“So, how has the tour been going,” she asked.

“Great.” You smiled and Dean smiled back. “We just have Tokyo for a few dates after this. Then it’s back to reality.”

Dean laughed. “Not quite babe. Remember? You’ll be moving things into my place.”

You blushed at the realization that Dean was serious about you moving in with him. “Yeah. True. That will take some time to get used to.” You hadn’t lived with someone in so long. 

Sam and Cas came in and joined the conversation. Both Cas and Sam hit it off well with Belinda. She then joined you for Dean’s soundtrack, then you all ate dinner before the meet and greet. 

The Meet and Greet went as expected. There was always one or two groupies wanting Dean to sign their breasts, but finally Dean refused. “I’m sorry I can’t sign breasts anymore. I’m dating someone and I feel it disrespects her to do that.” He smiled over at you and couldn’t believe he just defended your relationship. 

Dean was incredible as usual. Belinda watched the show in awe, almost as much as you. You watched the way he sang and gyrated his hips and you blushed knowing you knew how good he was in bed and used those moves to his advantage.

After the show Belinda joined you at the penthouse suite in the five star hotel. She was given what would have been your room as you and Dean retreated to his room for a long night amazing sex.


	9. Chapter 9

The next two days in Sydney were amazing. Belinda took you, Dean, Sam, and Cas to all the touristy and non touristy spots to visit. You and Dean looked like an average couple. Dean was dressed down in lounge pants, t-shirt, hoodie and hat and so did you which made you look like any other touristy couple and kept the fans from bothering you. Dean was recognized a few times, but most fans were respectful and did not cause an ambush. You and Dean enjoyed having some romantic PDA moments, kissing at a romantic site or holding hands. 

You were at the Sydney Opera House when your work phone vibrated in your pocket. “I need to get this.” You stepped away. “Hello.”

“Hi. This is Yvonne Lee with BAB calling to confirm an interview with Mr. Winchester on Thursday.”

Thursday was in two days, but Dean was supposed to have the entire week off. “I don’t recall that being in our itinerary.”

“We were confirmed months ago,” Yvonne said.

“Hey Sam.” You got Sam’s attentions d he walked over. “Do you recall Dean being confirmed for an interview with BAB?”

“No.”

“What is BAB?” You inquired to Yvonne.

“Busty Asian Beauties Magazine. Mr. Winchester is a long time subscriber. We’re having a celebrity issue and he was selected to be interviewed,” Yvonne said.

You called Dean over. “Hey Dean. Do you recall granting an interview with Busty Asian Beauties while in Tokyo?”

“No, but I’ve read all their mags.” He smirked. You knew Dean read that magazine, as you found some stashed in his suitcase, but you were OK with it if it kept him celibate for you and stopped him from sleeping with groupies.

“You have an interview this Thursday.”

“I don’t recall agreeing to it.” Dean looked sincere as he said it.

“You must have.” Not wanting Dean to miss any commitments while you were his tour manager, you agreed. “We’ll go.”

Dean looked sad.“You shouldn’t have to miss time off from hanging with your best friend, just to come with me.”

“It’s my job Dean.”

“But I don’t need to do it anymore. I have you.”

“You need to stick to your commitments Dean.”

That night in your hotel bedroom, you and Dean talked in bed. You decided together that Dean would go ahead fly to Tokyo with Sam and Cas, and you would meet up with him on Saturday. “You stay here in the suite with your friend, then meet up with me.”

“You sure Dean?”

“Yeah. You deserve to spend some free time with your friend and without me. I’m sure you are more than sick of me by now.” 

“I’m not sick of you. In fact, I love being with you, but maybe you’re sick of me.”

“Hell no baby. I’m going to miss every inch of you.” Dean kissed you, setting a fire to your belly as he rolled you to your back and kissed down your body saying how much he will miss each body part of you. “I’m going to miss your beautiful face when I wake up and go to bed.” He kissed down to your neck. “I’m going to miss this spot right here.” He nipped your neck and you moaned. He continued to your shoulders, then down to your breasts. “I’m going to miss these so much.” He puckered is his lips over swirled his tongue around the nipple and on the other breast, repeating the process. He then moved down your torso to your inner thigh and began nibbling between sides. “I’m definitely going to miss this beautiful sight and how wet you get for me baby.” You moaned. He licked your slit, splitting your lips and you grabbed the sheets. “I’ll miss your taste. I don’t know what to do if I can’t taste your sweet pussy for a few days.” He continued working his tongue in you. You had to push and keep him away after your orgasmed as he kept going. “I just love this so much.”

“Dean. I can’t.” You were crying in pain from the overstimulation. Finally slotting between your legs, he spent the rest of the night making love to you until you both crashed exhausted.

The next morning, you kissed Dean passionately before he, Sam and Cas climbed into a taxi. “Text me when you get there Dean.”

“Of course Baby. I will. See you in a few days.”

“I’ll be there Dean.” You smiled as you watched the cab take off. 

Knowing Dean was probably doing manly things getting drunk, going to Cabaret or Geisha Girl shows with Cas and Sam, you and Belinda had a spa day. You had everything waxed, a deep vagina steam, a mud bath, then a float pod spa session. 

You felt like a brand new woman. On Saturday, you hugged Belinda and smiled. “It was so good to spend time with you.”

“You too. I like Dean. He seems to be good for you.” Belinda smiled. 

“He does.” You smile.

I love him.” You hugged her one more time as you got in the cab to head towards the airport. 


	10. Chapter 10

**Summary for the Chapter:**

> Sm

You pulled up to the five star hotel in Tokyo excited to see Dean. You hadn’t heard from him since he texted you to let you know that he was in Tokyo and you didn’t bother him giving him space and time to hang with his brother and best friend. You were excited to strip down for him, showing your new lingerie and your hair free, soft, clean body. You walked up to the front desk where you were given the key Dean left for you. Leaving your bags with a bellhop, you headed up to your room to surprise Dean. As you were going up in the elevator, something didn’t feel right. You couldn’t understand why, but all of a sudden you were very nervous to see Dean. 

You got to the penthouse floor, stepping directly into the suite. The place was an utter mess. Liquor bottles and clothes were strewn across the room. You were immediately put on defense thinking they were robbed. 

You started heading towards the master suite. You began hearing weird sounds coming through the door. As you approached the sounds got louder and you thought there was a struggle. _ Dean. _You put your hand on the knob and wondered if you should open it. The sounds were getting louder, grunting and a higher pitch whine. Something was off. You opened the door and gasped at the site in front of you. Dean was on the bed while one very busty Asian “beauty” was giving him a blow job while the other rode his face as he fondled her breasts with her hands on top of his. 

Heat rushed to your face in anger and embarrassment. Just then, both women turned around giving very smug smiles. You could barely see Dean but the woman, who was riding his face, raised herself enough for you to see him. He looked completely zoned out… blissed out. You shut the door quickly and loudly and stood there as you hands balled up into fists and your eyes betrayed you by stinging with angry tears. 

_ How could he after all this time? We were together; he wanted me to move in with him. He said he loved me. Who just throws that away? _

You didn’t know what to do. You just stood there staring at the door for what felt like too long. Just then you heard the bellhop opening your room door, bringing you back to the present. You rushed over and stopped him, handing him a twenty dollar bill. “Take these back down to the front desk now, please.” He turned and rushed back towards the elevator.

As you searched the room for stationary, you saw Cas naked and passed out on the floor near the sofa while Sam was naked and unconscious on the sofa. 

_ How could they have let him do this? They liked you. At least I thought they did. _

You were hurt beyond words. Your body went into angry autopilot. You grabbed some hotel stationary from a nearby desk and quickly wrote Dean a note. 

** _You mother fucking asshole. I trusted you. I really thought you had changed. Hell! I loved you, and I thought you did too. I thought we had a future, but you were just lying to me. I can’t believe you just threw our love away for a fuck. You are a sonofabitch. You can fucking deal with the rest of your mother fucking tour. I’m out of here. Never fucking call me, text me, or come to my door ever. Y/N_ **

You taped the note to Dean’s bedroom door.

You hurried out the room back down to the to the front desk, turning in your key, and hailed a taxi heading back to the airport. At the airport, you typed up an email resignation letter to Chuck Shurley, 

** _Mr. Shurley… I mean Chuck,_ **

** _I am writing this letter to inform you that I am resigning from the Dean Winchester tour and Heavenly Records as of today due to irreconcilable differences with the artist. I’m truly sorry I could not maintain my duties for the duration of this tour, but I felt my physical and mental health would be in jeopardy. I no longer feel I can actively work at your label anymore. I do appreciate the opportunity to work with your company and for the education I received while working for you. Unfortunately, I will be unable to assist with the training of my replacement. With humblest regrets, Y/N_ **

You read the email a few times, then hit send as you got up right as boarding began for the first available flight back to the US. 

You flew back to St. Louis in fifteen hours, not sleeping once during your flight, even having a first class sleeping seat that reclines and elevates your legs. You then took an Uber home. You left your luggage right inside the door in the living room, walking back to your bedroom, shutting the door. Stripping down to your panties, you threw on a sleep shirt and crawled into bed. The tears of pain, loss, and humiliation finally hit as you cried yourself to sleep.

**Notes for the Chapter:**

> Sorry it took so long to update. I had some writer’s block lately. I can’t wait to show you what’s next. I hope you enjoy.


	11. Chapter 11

Dean awoke the next morning naked with a splitting headache and no idea how he got that way. He looked around and saw his clothing scattered all over the place, but no one else’s. He looked at his watch. “Y/N should have been here by now. Y/N?” He called her name. He got up, putting on a pair of lounge pants and headed to the bathroom. None of her suitcases set in the room and none of her toiletries were scattered across the bathroom counter as usual. He did his business, walking out of the bathroom, putting on a t-shirt, and walked out into the living room. Sam and Cas were just coming to, both having splitting headaches and were naked as well. Sam covered his genitals with a pillow and Cas reached out grabbing his trenchcoat and covered himself.

“What the hell happened?” Dean looked around at the mess. Liquor bottles and clothing were scattered across the suite.

“I don’t know,” Sam shook his head.

“Cas?” Dean looked at him. 

“The last thing I remembered we were at the BAB headquarters for your interview.” Cas recalled.

“Me too,” Sam said.

“Me also.” Dean looked around. He went back to his room to his suitcase and looked. All his money and jewelry had been stolen. He walked back out of the room. “We’ve been robbed.”

“What’s that?” Sam noticed something taped to the wall.

Dean turned and saw the note on the bedroom door. He walked over, grabbed it and read it. His eyes began to prickle with tears. “Y/N was here and left very angry, but I don’t know why.”

Sam looked at the letter Y/N left, then as he looked around, he saw a note affixed to the TV stating, “watch this DVD” with a DVD placed on the DVD player. 

Sam walked over turning on the TV, placing the DVD in the player, and hitting play. The video starts with them entering the room with four very Busty Asian Beauties. The DVD cut to Dean’s room first showing him with one woman giving him a blow job and the other riding his face. He then saw Y/N open the door as the women turned around and Dean’s eyes were glazed over. The video then switched to the living room where both Sam and Cas and the other two Busty Asian beauties were in one big orgy. Sam was slamming into one of the women from behind while she gave a blow job to Cas and the other woman was riding Cas’ face. Then they all switched positions. They all watched the video mortified.

None of them could remember anything that played on the video or how they even got back to their room, even after watching the video. “Is this even us?” Sam asked. “Could be doppelgangers.”

Dean felt disgusted. “Y/N will never believe that I didn’t do this. I’ll never get her back. It’s not doppelgängers. It’s us and we were roofied,” Dean said aloud.

Sam and Cas both agreed.

The note next to the DVD said. 

** _There is more than one copy. I want Twenty million dollars wire transferred to the following account number by ten am on Tuesday or TMZ runs the story. You can kiss your singing career bye and be the next big pornstar instead. You have the money, so don’t pretend you don’t or can’t get it. You are a lying bastard Dean Winchester. You strung me along for all these years, fucking me when you felt like it, then this time chose another woman, letting me go like trash. You’re finally gonna get what you deserve. _**

Dean recognizes the writing as Kim Lee, aka Yvonne Lee a former fuck buddy that he slept with on and off for a few years when she came to America for modeling. She never made it in the modeling world, went back to Tokyo joining Busty Asian Beauties. He never considered her a girlfriend or a commitment but a friends with benefits when he felt like it. She, however, thought there was more. When he first saw her yesterday at the interview, he knew he should have stayed back with Y/N. He answered her questions but wasn’t his usual flirty self. He remembered her asking if he was dating anyone and he said, “I’m dating this incredible woman, Y/N, who also happens to be my incredible tour manager. It took us two months to get together but we’re perfect together and I’ve asked her to move in with me when the tour is over.” He remembered drinking wine at the interview as he was accustomed to doing. His brain focused on the day in Tokyo and he realized whether he was wrong or wronged he probably lost Y/N for good. 

Dean decided to contact Chuck Shurley with Heavenly Records and cancel the last few nights of the tour while he decides what to do.

Dean was ready to fight for his life and for Y/N back. “I’m not paying that bitch. I’ll go to the hospital right now and get tested for rape drugs and file a police report right now. I love Y/N and she’s gone because of what Kim Lee did to me.”

Chuck agreed to let Dean fight the extortionists. He referred Dean, Sam and Cas to the hospital. At the hospital, they were subjected to bloodwork, rape kits and tests to determine if there was female secretions on them. Dean, Cas, and Sam jointly filed a police report providing the police with the DVD and blackmail letter. They stayed in Tokyo while the police made their investigations.


	12. Chapter 12

You awoke to fifty missed calls and texts from Dean, Sam, Cas, and Chuck Shurley. You blocked all their numbers, never wanting to hear from any of them again.  _ I told him to never contact me again. _

You got up and padded to the restroom. Your eyes were bloodshot from crying so much; your heart ached at losing Dean.

You were taking a nap on your couch that afternoon, listening to the news when you heard the newscaster talking. “Today, pop star Dean Winchester has cancelled the last few shows of his world tour stating he was drugged and raped while in Tokyo by a former girlfriend. We tried reaching out to our local Tokyo affiliate but due to the impending investigation, they could not respond to our inquiry. We have also tried reaching out to Mr. Winchester’s people, but have received no comment on the matter. Mr. Winchester has been on tour for the last six months. We’ll keep you abreast on anything recent. Just follow us on…” You tuned out the rest of the commentary. 


	13. Chapter 13

Dean pressed charges; his former girlfriend was arrested before the DVD got leaked; and he finally returned to the US. He moved back to his underground house, he called the bunker, with Sam and Cas in Lebanon, Kansas instead of his home in LA to keep from the nagging paparazzi. His next step in life was to try to get Y/N back. 

Dean called Chuck and begged him to release Y/N’s address so he could talk to her. “I need to see her Chuck. I love her and I want her back.”

Chuck smiled. “I just knew she was going to inspire you Dean. I’m glad you found her to share your life with.”

“I won’t be sharing anything if I can’t get her back. She probably believes I faked the rape.” Dean was distraught.

Chuck said the same thing Cas and Sam already said to him. “I think if you are sincere, she’ll believe you are sincere.” 

Dean proclaimed. “I’m going to win her back.”

Chuck texted Dean Y/N’s address and phone number.

——————————————————

Back home, you were trying to get back to a semblance of normal, before you were hired for this tour, before Dean Winchester. 

You tried going to the gym again and hanging out with friends. Most of your friends were dating someone and always wanted to set you up on a blind date with one of their male friends, but you didn’t want to to be setup. “I’m not ready for a relationship.”

They all came back with,“Why?”

“Because I’ve been on a tour for the last three months with this guy, his brother and friend. I need some time alone.”

Belinda was the only friend who knew about your relationship Dean. Everyone else thought you were just a recluse for not wanting to find someone, but you didn’t want to tell them why. 

Belinda was the most shocked about what you saw inTokyo. “He loved you Y/N. I could see it and feel it between you. I believe he maybe telling the truth.”

“Everytime I try to sleep I can’t get what I saw out of my head. Them touching him; Her riding his face; he looked like he was enjoying it.”

“But if what he said is true he was drugged, he could have been hallucinating, thinking you were the one giving him pleasure.”

She had a point. “I guess that could be true.”

You weren’t sure what to do. _ Do I talk with Dean and take him back or not. _This was your decision.


	14. Chapter 14

Two months passed and Dean decided to try to get Y/N back. He sat down and talked with Sam and Cas. “I want to get Y/N back.”

”Are you sure Dean?” Cas was the first to speak. “I know you love her, but she said to never contact her. I just don’t want you cause yourself more trouble.”

“I love her Cas.” Dean was angered. “I know what happened but I want to try to get her back.”

Sam looked at his brother. “I know you want her back. You guys were great together. I’m not going to talk you out of it. I’ll support you either way.”   


”Thanks Sam.”   


Cas looked at Dean. “You have my back too. I just have to give you the risks or I wouldn’t be a good head of security.”

”True.” Dean chuckled. He walked down to the bunker’s garage where his car collection was. He had a 911 Porsche, an older Jaguar, new Ferrari, new Cadillac Escalade, A couple of old trucks from the 1930-1950 that came with the bunker and new and old Harley-Davidson motorcycles, but he decided to settle on his first car, his dad’s car, a sleek black 1967 Chevrolet Impala. He remembered his conversation with Y/N about cars one night while they were on the bus between Adelaide and Sidney. They were talking about their firsts. 

_ You smiled. “I’ve always loved fast cars. My first car at sixteen was a 1981 baby blue Mustang with a sunroof, hatchback and louvres.”  _

_ “Nice,” Dean smiled. _

_ “And yours?” You looked curious. _

_ “I had a 1967 Black Impala. It was my dad’s car; I drove it when I was sixteen and then he passed it down to me. I still have it in my car collection.” _

_ “Nice, sexy car. Does it still run?” _

_ “Hell yeah it does. I work on it during my downtime when I’m home, then take it out for a few spins or to a few charity events to keep it running. She’s still a complete badass. She’s my Baby.” Dean grinned. _

_ “Sounds sexy and you behind it, even sexier.” You smirked straddling Dean’s waist as you leaned down towards his lips. “Maybe we can take it out for a drive, pull over, and check out the big back seat someday,” you said with a smirk as you kissed him passionately, then grabbing his hard cock, you lined it to your entrance and lowered yourself on him.  _

_ As he fondled your breasts and you rode his cock, he smiled. “I can’t wait to see you, especially like this in the back of Baby.” _

_ You reached down massaging your own clit with your thumb as you viced around Dean. “Fuck Yes! Yes! Yes!” You collapsed against him and nestled your head in the crease of his neck, peppering his neck and shoulder in kisses. “Damn Dean! That is such a turn on. I’ll ride you so fucking hard in that car.” _

_ “Wow! I never knew a woman get so turned on by fast cars.” _

_ You began undulating your hips against his soft cock, making him hard again. “You have no idea how much I want to fuck you in a back of your car right now.” _

_ Dean began to groan. “I can imagine. Fuck! You have no idea how hard I want to pound you into the mattress.”  _

_ “How hard are you?” You laughed at your comment.  _

_ He chuckled. “This much.” He rolled you to your back, thrusting into you hard as you cried out his name with each thrust.  _

Dean looked at his car. “We’re gonna get her back.”


	15. Chapter 15

It was two months later since you returned home from the tour, from Dean. You were back at your house that you rarely lived in before, always on the road with some band or musician. It didn’t really feel like home to you. You looked at all your music memorabilia and your baby grand piano and wondered what this all was for. You only knew Dean six months but it felt like a lifetime. He became your home over those two and a half months. 

Now, not only did you have no job, no romance, no life, but now you have positive pregnancy news you just received from the doctor twenty minutes before. You had been feeling run down, lethargic, and nauseous recently. You decided to see your doctor, thinking you were probably depressed. While you were dealing with clinical depression, you were also six weeks pregnant, realizing you conceived the baby with Dean in Venice when you both confessed your true feelings towards each other. You began to cry, sobbing, remembering your life with Dean. You didn’t think about birth control with him. You both just wanted each other, needed each other desperately at that moment, not thinking about the consequences. Now you have another life growing inside you and the man you thought you loved sleeping with other women. 

You heard a muffler sound outside. Figuring some kid got an old car and decided to speed down the road letting everyone hear his old car, being all machismo made you laugh. 

You then began to cry thinking about Dean and his love of old cars. Curled up on the couch in the fetal position, you were falling asleep when the doorbell rang. 

You got up, absentmindedly rubbing your abdomen. You walked over to the door, still rubbing your belly as you opened your door and gasped. Dean was standing on the other side. 

“What are you doing here?” You were angry.

Dean took a step in.“I didn’t do what you think I did Y/N.”

You furrowed your brow and scowled at him. “What I think you did? What I know you did. You were fucking two women at once.”

“I was drugged Y/N.”

“Yeah right. You were drugged.”

Dean looked at you as tender as he could. “Y/N. I love you. I didn’t and wouldn’t have thrown our relationship away. I promise. I didn’t just ask you to move in absentmindedly. I’ve never been in this kind of relationship before. I’ve never wanted to share my life with someone else until I met you. From the moment we met, I was drawn to you, and the first time we made love and you thought it was a mistake, it wasn’t. I never felt so alone in my life until I got to Europe. You make feel whole. When Italy happened, my whole world changed. I realized you were the one I want to spend the rest of life with. I love you.”

You stood back. Your heart was hearing everything he was saying. You closed your eyes to breathe while your brain reminded you of what you saw. You just kept seeing them, the one taking him in her mouth while the other one rode his face. You remembered when you did that with him and how he felt. You believed he did get pleasure from her. She was his ex. He had feelings for her before. You shook your head. You didn’t believe him. “I can’t Dean. You need to leave.” You tried to push him out the door. 

Dean held the door open. “Please Y/N. Let’s talk about it. Please!”

“No. I can’t do this Dean. Please just leave. I can’t do this.” You shut the door on him, locking it and leaning against the door, tears rolling down your face. 

Dean knocked on the door. “Y/N. Please. I just need to talk to you. I need to explain.”

“Just leave Dean,” you yelled from behind the door. “I just can’t. Can’t you see this is tearing me apart? I can’t do this in my condition.”

You heard Dean “Condition? Wait. What condition Y/N?”

You couldn’t answer. You were crying so hard that you were gasping for air.

Dean continued knocking. “What do you mean?”

You couldn’t stay like this. You tried to hold back the tears and spoke loudly. “You need to leave right now before I call the police. Just go.”

Dean leaned his forehead against the door; tears stung his eyes. “Y/N. Don’t do this.”

“I said go,” you yelled.

“OK. I’m going, but I’ll be back and I hope we can talk then. I still love you.”

Your eyes were sore from crying so much, but you couldn’t stop. You heard the car with the loud muffler startup. You went to the window and lowered a blind, peaking out. Dean was inside a slick black Chevy Impala. His car was the one you heard. You saw him pull out and take off down the road. You couldn’t stop the sobs, gasping for air as you went to the couch, laying down, wrapping your arms protectively around you as you cried so hard your eyes and throat hurt. 

———————————————————-

Dean drove to a local hotel nearby Y/N’s house, so he could be close enough to continue trying to get her back. He called Chuck. “She said something about ‘her condition’. What condition is that?”

“I don’t know Dean. I’ll look into it.”

“Please just let me know. Is she sick? Is she dying? I worry about her Chuck. I love her too much to lose her.” Dean stayed in his room and thought about what Y/N said.


	16. Chapter 16

The next morning, you called Heavenly Records. 

“This is Y/N. I need to speak to Mr. Shurley please.”

The receptionist transferred the call. “Hey Y/N. This is Chuck. What can I do for you?”

“I need to ask for my job back please,” you said solemnly. 

“Of course. Everything OK?”

“Well, I need to get my insurance back. I need to be honest Mr. Shurley.”

“Call me Chuck please.”

“Well Chuck, I am about six weeks pregnant and need to keep my job. Was wondering if you have a job that I can work for the next six to seven months and then go on a long maternity leave.”

“I don’t mean to be nosey but would this be Dean Winchester’s baby?”

“Yes Chuck, but I don’t want him to know or at least not yet. I can’t even face him right now. You said I’m a good worker. I just want to go back to work to get my mind off things.”

“Absolutely. In fact, I know just who to place you with.”

“Please no more male performers at this time.” You didn’t want to deal with men this time.”

“No males. In fact, I think you should work for Donna Hanscum. She’s an up and coming artist on her first co-headlining tour opening with Charlie Bradbury. You’ll be working with both artists.”

“Sounds great.” You smiled. You were going to get back into the game. “Thank you Chuck.”

“Tour starts in two weeks. Is that enough time for you get it together and get a doctor's clearance?”

“Sure.”

“Good to have you back, but if I may speak personally Y/N, I think you need to tell Dean.”

“I know sir, but I just can’t right now. You don’t know what really happened and the wounds are still too fresh.”

“I know more than you think I do, but I understand.”

“Thank you Chuck.”

“You’re welcome Y/N.”


	17. Chapter 17

Working with Donna and Charlie was a totally different experience than with Dean. They were pure professionals. They were also new to the music and touring game and weren’t jaded like Dean was. By the time you met Dean, he was huge with Yes men and groupies, by the dozen, before you. Your first encounter with him was the first time someone rejected his advances and it changed him. You changed him. You thought for the better. 

Donna and Charlie were humble and hard working. They also knew your condition and knew you would need downtime, as Donna was a mom herself and brought her husband Doug and her daughter Bree with her on tour while Charlie brought her partner, Dorothy. You even got along with head of security Jody Mills. 

The tour was going great. Both Donna and Charlie made it to interviews and meet and greets on time. They were kind and humble in interviews and with fans. The tour was going by quickly. 

In Boston, you went and had your first ultrasound on your day off. Your doctor had scheduled the appointment with his former roommate from med school. You lied on the table while the technician ran the wand over your belly. Everything looked great. The size of the baby was good, even though you had lost weight. You saw the doctor and were given medicine to alleviate the nausea and help you put some weight on. Everything was going good. 

From Boston you went south to Charlotte, Atlanta, and a few shows in Florida. After that, it was New Orleans, Nashville, St. Louis, and finally to Kansas City. 

It was in New Orleans when you heard the news: Donna co-wrote and recorded a duet with Dean Winchester on her current album and as a way to boost ticket sales, Dean would be joining her onstage to perform that duet in Kansas City.

“I can’t talk to him Donna.” You were crying. “I still can’t face him. I still see the horror in my head when I hear his name.”

Donna hugged you and sat you down. “I am close friends with Dean and even I know he’s a flirt and has groupies by the dozens, I also know he cares for you. He came to me after the tour and told me everything. He loved you. He said he wanted you to move in. He doesn’t even have the groupies anymore. He wouldn’t have pressed charges against Kim Lee if he participated in it, but he didn’t and I believe him. I met Kim a few years ago when Dean and I were co-writing music. She was an insufferable bitch. She was always nagging on him about something. I guess the sex was pretty great because he stuck with her. She was a pornstar and nude portrait model (trash mags), but she was horrible to him. He also said how amazing you were with him. He said you put him in his place first off and he loved that about you. He said you rejected him and that made him strive to be better. He loves you. If he knew he was going to be a father, he would be so happy. He loves playing with my little girl and is totally great with kids.”

You listened to what Donna said. Your heart melted and your stomach flopped in a good way hearing her talk nice about him and how he felt for you and for kids, but you still had that sickening feeling in your stomach. “I just don’t know Donna. I just get sick at the thought what I saw.”

Donna looked at you. “I’m sure that was horrific and I’m not going to push you to see him if it will stress you out. That is not good on the baby. If you need to go away for that show, I understand. I just hope you will give him a chance.”

You had three more shows to decide. “I’ll think about it.”

“I’ll be here for you.” Donna smiled. “Either way.”

That night in the bus traveling from New Orleans to Nashville, you dreamt about Dean.

_ You were on the red carpet for some musical event. You and Dean were married; the diamond ring on your finger beamed but paled in comparison to both yours and Dean’s smiles. You had a beautiful toddler boy that looked just like Dean, and you were very round with baby number two, like nine months round. You remember Dean in his dark maroon suit and tie as he stood behind you, his head tilted to the side smiling at the cameras; he had his hands on your stomach. You were blushing. The reporters and paparazzi were asking absurd questions like when you were due or do you know the sex, but Dean would tsk them away. You held your belly walking towards the event. Dean helped you sit down and your son sat next to you on one side while Dean sat next to you on the aisle. He grabbed your hand and you held hands during the show. Finally, the award that Dean was nominated for was announced. You gripped his hand tight, as nervous as he was. Your son was getting antsy in his seat. You calmed him down and held his hand too. _

_ “And the award goes to…. Dean Winchester.” _

_ Dean smiled huge leaning in and kissing you passionately. He then grabbed his son, who wanted to go up with him and they walked to the stage. Once onstage, Dean put his son on his shoulder and held his award. “I want to thank God, the academy, Mr. Chuck Shurley of Heavenly Records, my producer, my band, but most of all, my beautiful amazing wife Y/N, who stood by me during a very trying time for both of us, for being an amazing muse, for giving me this little rascal, and for our child that is coming very soon.” _

_ You smiled and clapped with the audience. Dean went backstage for his interview. When he and your son returned, he came back to your side. You started to get up and stopped. “Oh shit! My water just broke.” _

_ Dean got up, holding you as he helped you out of the row. You clutched your stomach and moaned. “Oh man Dean. He or she is ready now.” _

_ Dean picked you up bridal style, like you weighed a feather as he carried you out. An ambulance was already outside as he and helped you in and you were rushed to the hospital. _

_ You then skipped to screaming with sweat pouring from your forehead as you were pushing your baby out. “Push baby.” Dean smiled, holding your hand, trying not to admit you were almost breaking his hand. “You’re doing great.” _

_ “You squeeze a watermelon out of an eye dropper.” _

_ “I love you Y/N.” _

_ “I love you too, Dean.” You cried out again as the doctor said, “I see a head.” _

_ You pushed again. Another push and the doctor raised the baby up. “It’s a boy.” _

_ “Another boy?” Dean smiled. “Oh man Baby. This is great. Thanks.” _

_ You smiled as you watched Dean cut the umbilical cord. The nurses cleaned your son and put him in your arms. _

_ Dean kissed your temple. “He’s beautiful and you’re beautiful baby. Great job.” _

_ “Thanks. You weren’t so bad yourself. We did great together.” You saw Dean leaning in so you closed your eyes felt him tenderly kiss your lips. _

You awoke smiling, thinking of how great he was in the dream which made you remember how romantic and tender he was when you were with him. Maybe you could talk to him. You still had time to think on it, but your dream made you want to talk to him more.


	18. Chapter 18

The next day in Nashville, you told Donna your dream. “Gosh. That sounds promising eh?”

Her Minnesota accent coming through.

“I guess. It was so surreal. I literally woke up smiling.”

“So, does it mean you’ll talk to him; give him a chance?”

“Maybe.”

The Nashville show went really well and St. Louis too. In St. Louis, you had family and friends visit since this was your hometown. You got them VIP tickets and they got to hang with you, Donna, and Charlie before the show. You were starting to show since your were almost five months pregnant now, but you covered your pregnancy with a flowy dress, so no one was suspicious, even when you had to excuse yourself to the restroom to vomit, claiming you had the touch of the stomach bug. Your family and friends visited you awhile after the show and then you climbed on the bus to go to Kansas City. 

Your nerves were eating at you overnight during the drive between St. Louis and Kansas City. You couldn’t sleep, watching stuff on your TV in your little bunk to keep from freaking out. You were hoping you could avoid Dean as much as possible, at least until after the show so if you became panicked, stressed, or angry with him, you could just leave. 

When you arrived at the venue, you went and took a shower. You stood under the water, using your loofah across your body. You rubbed your hands over your pregnant belly, daydreaming of Venice when Dean made love to you after the initial lust of the sofa. 

_ “You’re so beautiful Y/N,” Dean said hovering over you, his lips peppered your neck in kisses, he was dipping two fingers in your entrance while his thumb tapped your clit. _

_ “You’re gorgeous Dean,” you said breathless and panting. “I’m getting close Dean.” _

_ He then pulled his fingers out of you and his thumb away from your swollen clit as he slotted between your legs. “I love you.” _

_ He stared into your eyes, the green of his eyes sparkling. _

_ “I love you too.” Your eyes swooned at him. He pushed himself in you, slowly filling you. _

_ He kissed your lips as he began thrusting in you at a moderate pace. Soon he was pounding you into the bed. You felt your walls cave as he pulsed inside you and released. With your eyes closed, you saw white and fireworks behind your eyelids as your orgasm hit. Dean filled you with his seed as he kissed you passionately; your hips were still grinding together as you two worked through you orgasms. _

_ “God, you’re beautiful.” Dean looked down at you; your hair was sweat soaked, sticking to your face while the glistening sweat on his face just made him more gorgeous. _

_ “You’re the beautiful one.” You looked at him. _

_ “Don’t ever think you are not beautiful. You are the most beautiful woman to me.” He stayed in you as he turned you to your sides and pulled you near him, wrapping his arms around you protectively as you both fell asleep. _

As you rubbed your belly, you talked to your unborn baby. “I love you little one. Whether me and your daddy get back together or stay together, I will always love you.” Just then, you felt the baby kick and you beamed. 

You got out of the shower and put on another flowy dress and headed to the dressing room. Walking in, you saw Donna, Doug and Bree on a couch, Charlie and Dorothy on another couch, and Dean sitting on the only loveseat left empty in the dressing room. As soon as he saw you, he stood up and stared. “Y/N.” He swallowed.

“Dean.” You looked at him, mouth was parched. 

You stared at each other, both pining. 

Dean finally smiled. “You look amazing Y/N.”

“Thanks. You too.” You meant it. He always looked amazing in a pair of jeans, a t-shirt, and a plaid shirt. The baby kicked and you absentmindedly pressed your palm to your abdomen. 

Dean immediately noticed that. “Y/N. You OK?”

Donna, Charlie, and Jody all looked at you wondering if you would tell him. You just stood there a moment when finally Donna grabbed Doug and Bree, while Charlie and Dorothy stood up. “I think we’re going to get some food so you guys can talk,” Donna said as they all left.

You stood there watching everyone get up and leave the room, except Dean. As soon as they left the room Dean repeated himself. “Are you sick? You said something about a condition when I saw you last.”

He remembered what you said to him when he showed up at your door and you sighed. “Yeah. I just have some stomach issues.” You weren’t sure you wanted to tell him a baby at this moment before he goes on stage. 

“Are you going to be OK?” Dean seemed genuinely concerned.

“Yeah. I will be better but it might take another four to five months.”

“I’m sorry.” Dean looked concerned you were sick. 

“It’s OK.” Your breath hitched. “It’s not as bad as you probably imagine.”

“I miss you,” Dean interjected as he stared at you.

“I miss you too Dean, but I still can’t get that memory out of my head sometimes and it hurts me to see you.” You looked at him trying not to remember what you saw, but the man you fell in love with. 

“I’m sorry. I shouldn’t have gone to Tokyo. I didn’t want to. You told me to fulfill my commitments.”

You realized you pressed him to go to Tokyo, but you didn’t force him to drink and have sex. “Don’t start that shit with me. I didn’t drink a roofied drink and have sex with my ex.” 

“I didn’t mean that Y/N. I’m sorry.”

You swallowed, realizing you were just as guilty for what happened to him. 

Dean looked at you sincere. “It’s not either of our faults. It was hers.” 

Just then, the door opened and Chuck Shurley, Sam, and Cas walked in. Chuck saw you together talking. “Oh good. Are you excited about the baby, Dean?”

You glared over at Chuck while Sam, Cas, and Dean all looked dumbstruck. “What baby?” Dean finally asked.

You looked at Chuck who was giving you an encouraging smile.

You looked back at Dean. “The stomach issues I’ve been having is that I’m almost six months pregnant.”

Dean looked at you then doing the math. “That would make…”

“You the father.” You swallowed as you looked at Dean. 

He took a moment to process it. Then he began to smile. “A baby?”

“Yeah.” You looked down and smiled, as you rubbed your stomach. 

Sam and Cas still looked like a deer in headlights.

Dean looked like he was thinking, doing the math, then smiled. “Venice.”

“Venice,” you said with a small smile. 

“Everything I ever needed in this life started in Venice,” Dean looked at you. He moved in closer to you. Your breath hitched and you struggled with wanting to leave the room, but he kept slowly moving closer to you. “I want to be there for you and the baby. I want to be in your lives. I’m offering you move into my home in Lebanon once the tour is over. It’s called the bunker. It was passed down to Sam and I by our grandfather. It’s a storm shelter. I have a recording studio there. You’ll have your own room if you want; Sam and I will help build a nursery in one of the rooms. It’s one of the safest places in the world to be. I just really want you and my son or daughter to be safe.”

You looked at Dean and thought about his offer. “Thanks. It is a very considerate offer. I’ll think about it Dean.”

“Please do.”

You, Dean, Sam, and Cas joined Donna, Charlie and their families for dinner. Donna then did her soundcheck and Dean joined her. You were tired, so Donna, Charlie, and Jody told you to go to the bus and take a nap before the show. You were still nervous around Dean, but you were getting better around him. You laid down in your bunk and fell asleep thinking of living with Dean, Sam, and Cas. 

_ You dreamt you were in your shared bedroom with Dean. You were on your sides and he was slowly kissing down your very pregnant body; your body lost in the pleasure Dean was giving you. You felt and saw sparks of electricity with every touch and kiss of his lips. _

_ Puckering his lips over your breast, you felt his tongue lapping at the pebble as it hardened. “Oh Fuck Dean!” _

_ “Fuck Babe. I love how your body responds to me.” _

_ He continued kissing down your abdomen, around your hips, to your inner thighs, then he ate you out until you came hard. _

_ As he slotted between your legs, you began to grind against him as he pushed inside you. Two orgasms later, you got up, throwing on Dean’s plaid shirt, walking down the hall to the bathroom, stopping in the hall doubling over as well your water broke and a contraction hit. “Dean!” You yelled for him. _

_ Dean barreled out of the room naked and saw you on your knees doubled over in pain. “I got ya.” He ran back to the room throwing on clothes and grabbing a pair of pants for you. _

_ He rushed back to the hall. Dean carried you to the Impala, setting you gently in the backseat, then drove like a bat out of hell to the nearest hospital to have your first baby, a beautiful baby girl. _


	19. Chapter 19

You woke after the concert start time and Charlie had already been on the stage and Donna was currently on stage. You walked to the side of the stage and sat in the chair provided for you next to the sound guy. You were getting very tired lately and needed to rest more often. Dean walked over and stood next to you, placing his hand on the side of your chair, his palm resting ever so gently on your back, and you stayed like that while Donna was singing and performing. Sam stood on your other side and Cas next to Dean. 

“Ladies and gentlemen, I had the pleasure of writing and performing this next song with the amazingly talented and the amazingly good looking, Dean Winchester.”

Dean gently squeezed your shoulder gently. When you looked up, he winked then took the stage in his signature plaid shirt, t-shirt under, and tight faded blue jeans. “Hey Beautiful,” he flirted with Donna.

“Hey sexy.” You watched Donna smile at Dean. They sang their song “love in a brokedown Impala”. It was a solid rock song infused with blues and a little country. Dean gyrated his hips and Donna did too. At the end the crowd went wild. 

“Before we say goodbye to Dean, he wants to share our new duet with you called ‘because of you’.”

“This song was written for someone extremely special and I hope she knows it’s for her.” Dean looked over at you and your eyes locked. He walks over, sitting down at the piano, and begins to play a very beautiful classical piece demonstrating his true talent tickling the ivory. The song he played led into the beginning of the new song. 

Donna started singing first, then Dean came in on the second half. “I never knew I wanted love. Never knew it even existed…”

They began to sing the chorus, but while Donna was singing at Dean to make it appear they have chemistry, he was singing directly to you. “But because of you, my life is so much better. Because of you, you filled in all my holes. Because of you, you made me believe in forever. Because of you, you evened all my scores.”

You saw his eyes glistening, and you began to cry. He began the next verse. “You breathed the love into my lungs, you bled yourself to repair my heart. As long as you are with me, our worlds will never part…” 

Donna sang her part then they moved into their second chorus. “Because of you, I’ll never ever leave you. Because of you, I can say goodbye to a bad past. Because of you, I’ll have a lifetime to tell you, that because of you, my love will always last.”

You were sobbing by then, like most of the audience by the time you got to the bridge. “Our hearts will never break, as long as we’re together, our love will never die.”

After the song, Dean smiles and leaves the stage walking over to you, dropping to his knees, and put your hands in his. “I meant what the song says. I love you Y/N and I want to be with you.”

You were sobbing as you looked at him in tear soaked eyes. “We can try.”

He stood up and pulled you into a big, long hug. It was warm and tender. As you rested your head against his chest, feeling his heart drumming, his arms protectively around you, you felt home again. 

You finally pulled away as you looked into his eyes; both of you were longing for each other. 


	20. Chapter 20

After the show, you guys had an after party, but since you all had a few days off, you all left separately. Donna, Charlie and their families went to a local hotel, while you got into the Impala with Dean, Sam, and Cas and headed towards Lebanon to the bunker to have a trial period with Dean. 

When you pulled up to the bunker, you walked in with Dean as he showed you around. He then directed you to his hallway where he gave you a room two doors down from him. “I’ll be just two doors down if you need anything.” You were right across the hallway from a bathroom. 

It was late and you were tired. You smiled at Dean. “Thanks.” You closed your door and locked it. Changing into a sleep shirt and shorts, you climbed into the nice big bed slowly falling asleep. 

You had the same dream that you had during your nap that afternoon and you awoke needing Dean. Your pregnancy hormones had your body craving him, but your heart still felt concerned about Dean’s ability to be committed to only you. Getting out of bed, you padded down the hallway to his room and gently knocked on his door. It took a few minutes but finally the door opened to Dean in nothing but his boxer shorts. “I... I… I’m not sure why I am here. I just needed to see you.” You were nervous as you stared at his magnificent body, strong muscles, and sexy bowlegs. You looked down embarrassed, breathless, your arousal beginning. 

Dean stared at you breathless as well. He then moved in pressing his palms to your face as he kissed you passionately. Wrapping your arms around his neck and carding his hair, he wrapped his arms around you, pulling you flush with his body, his arousal poking you in your stomach. You pulled away from the kiss panting and looking into his eyes. He was the man you fell in love with, the man who has given you this gift of a baby and you want him. “I need you Dean.”

“I’m right here baby. Right here. Whatever you need.” 

“I just need all of you Dean.”

He reached behind him shutting his door, then reaching down around your thighs, he hoisted you up as you wrapped your legs around his waist. He carried you down the hall to your room, kicking the door open and carrying you over to the bed. Laying you down gently, he hovered over you, following you up to the headboard where he put his hand behind your head as your head hits the pillow. You wrapped your arms around his neck again. “Make love to me Dean. Make me yours again.”

He smiled. “I will sweetheart. If you change your mind or anything gets too much, let me know. I’ll understand.”

You pulled his face down to yours, capturing his lips, letting him know you didn’t want to continue talking. 

Clothes off, you first felt his fingers working you open, his mouth and tongue working your nipples. One finger turned to two, then three as his thumb gently tapped your clit until you clenched around him, seeing white. He continued until you clenched around him two more times, pushing him away from your overstimulated sex. “Fuck Dean. I can’t.”

He gave you a few minutes, then pressed his swollen cock to your entrance. “I love you Y/N.”

“I love you too Dean.”

He pushed himself inside you and you cried out his name, still overstimulated by the multiple orgasms. He started the pace slowly rocking in and out of you, that turned to a quicker pace as he thrusted deep into you. “You feel so amazing baby.”

“Yes Dean! Please. More.”

When you blissed around him again, he lifted you up and carried you to the wall where he held you up by your buttocks and pounded into you. You were crying out his name over and over as he released hard, filling you up. He peppered your shoulder in kisses. “I missed you so fucking much.”

“I missed you too Dean.” 

He carried you back to bed kissing and laying his head against your stomach, talking to his unborn child. “Hey Sport. I am so glad your mommy told me about you and she’s here with me. I love her and I’m going to love you too.” 


	21. Chapter 21

Awakened by one of the most intense orgasms, Dean peeked up from between your legs, mouth and chin glistening wet by your slick. “Good morning sweetheart, did you sleep OK?”  
“Until just then, but yes, I slept more than OK. Better than I have since Australia.” You smiled. “Thanks for that.”  
He moved up hovering over you. “You’re welcome. You hungry?”  
“Famished.”  
“I was too, but you looked so damn good enough to eat so...” Dean smirked.  
Slotting between your legs, you smiled. “But I can wait a few to eat.”  
“Me too since I just had a great snack.”  
He kissed you, pushing himself inside you, letting you adjust. “God. I wish I could just stay inside you all day.”  
You giggled. “I think we may find it difficult to move around.”  
“Let’s just stay here then.”  
“I think you should move.” He smiled as he began to thrust slow and deep until you were holding onto him, nails digging deep into his shoulders, drawing blood as he pounded you into the mattress until you came with a wail and he released with a grunt.  
“Fuck Babe.” He looked down at you.  
You smiled as you pulled him down for a passionate kiss.  
Dean got dressed and went to make breakfast while you dressed and joined Sam and Cas in the main room to eat. Dean made pancakes and bacon, and you devoured it.  
After breakfast, Dean took your hand and gave you a tour of the bunker. You went to the library where there were tons of old books to read, you went to his man cave to see his large TV set, a 45 record jukebox, a pool table, and recliners. You toured his home studio where he had a baby grand piano, guitars, drum sets and other instruments. He then showed you their home gym, then the firing range. Finally Dean showed you his garage where all his many classic and expensive cars were and Sam and Cas joined you. You ogled over the Porsches. You weren’t so in love with the Ferrari, Jaguar, or the Escalade, but you admired Baby, his 67 Impala, the most.  
“When you move in here sweetheart, we’ll take our time fucking in every one of these cars in here. What do you say?”  
“I say it’s our cue to leave,” Sam said grabbing Cas and walking away.  
You laughed and Dean walked over, pulling you to him. “I mean it Babe.”  
You smiled. “Maybe later and maybe only the Impala. The others seem too small for inside.” You pecked his lips.  
“Oh. Trust me. We can find a way, even if you just want to ride me as I sit in the driver’s seat, but maybe we can just do it on the hood then.” He winked.  
Walking back in the bunker, you went to Dean’s man cave where you curled up against him on the sofa to watch his favorite horror movies, All Saints Day. You slowly fell asleep feeling Deans warmth, his loving arms around you, and hearing the thrumming of his unfaltering heart.


	22. Chapter 22

Two days later of living like a real couple with lots of cuddle time and sex, you stood next to the bus with Dean, ready to climb in and finish out the last few weeks of the tour with Donna and Charlie so you could move in with Dean to share the rest of your life with him and have his baby. 

Dean had you pinned against the side of the bus, as your tongues fought for dominance in each other’s mouths until you ran out of breath. “I’ll miss you Dean.” You said breathlessly, smiling. “I’ll miss you too babe, and also this little one.” He crouched down kissing your abdomen. “Be good for your Mommy; OK little buddy?”

“We’ll be fine Dean.” You laughed. One more long kiss and you were back on the bus, waving and blowing a kiss at Dean from the window. 

“Wow! Someone has changed these last few days. Someone got a lot of something something.” Jody smiled cocking her eyes as she saw the blush creep across your face. 

“I was going to say something similar,” Donna said laughing. 

“Yes I did. Dean and I made up many times these last few days.” You smiled and blushed. 

“I’m glad you made up.” Donna smiled.

“It was difficult at first. I still saw that terrible scene in my head, but then I had a dream about how wonderful he was with good memories of when we were together that I wanted him. It only helped that my pregnancy hormones were running rampant and I just needed him to fuck the image out of my head.” You laughed. 

Donna, Charlie and Jody all laughed.

“And the baby news?” Charlie asked.

“I’m just glad he wants this baby too.” You rubbed your belly. 

“That’s good,” Charlie responded and everyone agreed.

You went to a Denver next and onto Salt Lake. Next stops were Las Vegas, then finally Los Angeles where Dean would be joining Donna on stage again to perform their duet. 

The bus drove straight through the night from Salt Lake to Las Vegas on Tuesday night with two days off Wednesday and Thursday, the show on Friday and LA finale on Saturday.

It was five am on Wednesday when the bus arrived at the Luxor. You went directly to your room and crashed. It was morning and you were asleep when someone knocked on your room door. You looked at your clock; it was nine am. You had just been asleep for four hours and weren’t sure you wanted to answer it. You got up, putting on a robe and walked to the door. Looking out the peephole, you didn’t see anyone. You turned around figuring they had the wrong room, so you laid back down. Five minutes later, you heard another knock. Frustrated, you got up, putting on your robe and went to the door.

“Room Service.” 

You looked out the peephole and saw a hotel waiter with his cart, so you opened up the door. “I have an order for waffles, syrup, fruit cup, milk and coffee.”

“I didn’t order anything.”

“You’re room 2613?”

“Yes.”

“That’s the room number listed.”

You started to get angry. You were tired and just wanted to go back to sleep. “I didn’t order anything.”

Then you heard it. “I did.” Dean walked out of your blind spot to and steps around the waiter. “I did Baby.”

“Dean?”

“Thought I would surprise you.”

You smiled as Dean started to walk into the room. He walked up, grabbing you into a warm embrace. You wrapped your arms around him and pressed your head to his chest. “I’m so happy you’re here.” 

Meanwhile, the waiter followed him in and Dean directed him over to the table as he held you. The waiter set out the trays, then Dean gave him a large tip, as he left the room and shut the door behind him. 

You stayed wrapped up with Dean until he finally pulled away. “Let’s eat while breakfast is still warm, then we can go head up to my penthouse suite.”

“You got the suite here?”

“Highest point in the pyramid.” Dean smiled.

You smiled, then you two walked over to the table, sitting down and having breakfast.

You chatted about the weather as you ate. Dean listened to you talk about the tour and things you saw. You listened to him talk about the bunker and his songwriting ideas.

“I’ve decided I’m going to record ‘Because of You’ and release it as a single.” He smiled.

“You are?” 

“Do you mind?” He looked at you with concern.

“No. I love the song Dean. It will be the wedding song of the next decade.”

He smiled. “Well maybe we should use it first then.”

You stopped mid bite of food, your mouth gaping open. “What?”

“Maybe we should use it first.”

You shook your head quickly and looked at him. “Are you saying what I think you are saying Dean?”

He looked up and smiled nervously. “Maybe.” He then saw the shocked look on your face as it is somewhat too soon. “Oh! You think I’m asking you to marry me this moment. I don’t mean immediately.”

You breathed a sigh of relief.

Dean almost looked sad. Then he smiled. “I was just hoping maybe this will work out. We have the baby and you’re moving in. Maybe it won’t be too long before we make it official.”

You smiled. He was thinking of the future which made your heart swell. You finished eating and packed up your bags. Dean rolled your bags to the elevator, put on his keycard as you headed to the suites. 

The elevator door opened into the suite. Cas and Sam were sitting on the sofa. “Hey guys.”

“Hey Y/N.” Sam waves, his head looking down at his laptop.

Cas smiled. “Hello Y/N and how are you?”

“I’m good.”

You walked over sitting down in one of the other chairs as Dean rolled your luggage to his room. He then returned, sitting next to you on the loveseat, placing his arm around you as you wrapped your arms around his waist and curled up next to him. 

“I’m glad you’re here Dean.”

“I’m glad I’m here with you. I missed you.” He rested his hand on your stomach and the baby immediately kicked. “Wow! He’s happy Daddy is around.”

“Or her. Remember?”

“Of course sweetheart.”

He leaned in and begin to kiss your lips tenderly. You reached up placing your palm on his cheek as your lips moved together. He wrapped his arms around you, pulling you to him.

You hiked your leg over over his thighs, straddling him, wrapping your arms around his neck, as he pulled you closer. Kisses got needier as his hands moved down to squeeze your buttocks. You began to rock against him, brushing up at the beginnings of his already swelling cock. Sam and Cas took that as a sign. 

“I’m going to go visit the city for awhile. You up for that Cas?” You could hear Sam say to Cas while your lips remained pressed to Dean, hearing him begin to grunt happily. 

“Yes. I will join you Sam.” You could hear Sam and Cas leave and close the door behind them. 

“Fuck I thought they’d never leave,” Dean growled picking you up and carried you to the sofa, gently pressing you down, slotting between your legs as he slipped his hand under the hem of your shirt. “I need you baby. It’s been almost three weeks.”. 

Clothes off, bodies pressed together, you were panting as he continued brushing your g-spot with each thrust. “Oh Fuck Dean! Yes!”

“Scream out my name baby. I need to hear you.”

You were close. You felt his hand tapping your clit as your walls closed around him. “Yes! Yes! Oh Fuck yes Dean!”

Dean heard his name part from your lips and lost it, filling you full of him as he leaned in and kissed you. “Fuck Y/N.”

You felt both your hips roll as you were slowing down your motions. “Oh Fuck! You are so amazing.”

Turning you to your side against the back of the sofa, he stayed in you as you kissed lazily, feeling his erection begin again. Next thing you knew, you were riding him, crying out; his hands squeezing your breasts as you pressed hard against his thighs, back arched, and wailed when you came. “Oh God. Oh yes Dean. Fuck! Fuck! Fuck!”

“Oh Fuck Sweetheart. You just know how to draw the fuck out of me.”

You crashed against him, nuzzling into his neck, peppering him in kisses. 

“I love you.” You felt his hand press against you back.

“I love you too.”

He pulled a throw down and covered your naked bodies as you fell asleep. 

An hour later, Dean carried you to bed where he spooned you and let you sleep. “You sleep baby girl and sleep for our baby,” he whispered, draping his arm over your waist, you held his hand and went to dreamland.


	23. Chapter 23

While you wanted to go hang out on the Vegas Strip that night, sleep kept you safe in Dean’s arms all night. You awoke the next morning with your head pressed against Dean’s chest, your leg draped over one of Dean’s strong thighs. 

You got up, walking to the in-room bathroom suite. Turning on the water, you waited for the shower to get warm. You finally got in and stood under the warm water as it massaged your muscles. You soaped up your hair with your eyes closed, working the shampoo in your hair and scalp when you felt hot breath against your neck and hands began squeezing your breasts. “Do you need help?” Dean nibbled your neck.

“I guess I could use an extra hand or two.”

“I can assist with that.”

Feeling his hand move over your breasts and squeezed, you moaned. Slowly, he moved his down your abdomen, down to your pussy, his finger slid into your wet folds. “Oh.” You were shocked by the intrusion. 

“Fuck Babe. You’re so tight and warm.”

He increased his pace as you began to pant. Slipping another finger in you, you began to writhe against him. Moving his other arm down and wrapping it across your waist, he held you there and fucked you with his fingers, feeling his erection poking you in your lower back as his lips nibbled your neck. 

You were getting close. “Dean. Oh God! Please. Just fuck me. I want to come around your cock.”

“OK baby.” He removed his fingers and you whined at the loss of contact. Turning you around, he pressed your back against the wall, hoisting your legs up, as you wrapped your legs around his waist and arms around his neck. 

“God. You’re so beautiful.” He smiled.

“Just please.” You begged him with your eyes. In one fluid motion, he pressed you down, sheathing himself to the hilt, and you immediately began to roll your hips. “Fuck! Keep going.”

He kissed you as he began to thrust; his hands held and squeezed your buttocks.

You were writhing against him, yelling profanities, and holding onto him as he increased the pace.

His lips were suckling a nipple when your orgasm came through white and hot, but Dean kept going, chasing his high. 

“Fuck! Please! Oh God!”

Dean pushed down on your thighs, changing the angle as he released thick ropes deep inside you. “Damn baby! Fuck! I love you and love fucking you.”

“Me too. I love you and love when you’re in me.”

You cleaned up and returned to bed for a short nap, then dressed, and headed out to the strip. It was a romantic time kissing in front of Bellagio Fountains, at the top of the Eiffel Tower of Paris, and at the top of the Stratosphere; holding hands as you walked or when taking the bike taxis; sitting next to each other at the slot machines and holding hands while you tried to win big; and being the one to blow on the dice when Dean was playing Craps. After a long day on the strip, you and Dean returned to the hotel room to make love and fall asleep. 

The next morning you were greeted to banging on the bedroom door. “Get up girl. It’s spa day,” Donna yelled from the other side of the door.

You were in the middle of Dean eating you out, a hand squeezing between breasts while you were trying to keep you voice down. 

“Oh God,” you whimpered as Dean had you close with his mouth around your clit sucking as his two fingers were hitting your g-spot. “Oh! Please! Please! Right there! So close!”

He tapped his tongue against your clit and you came hard squirting all over his face as you were arched seeing all white and your body on tactical overload. “Fuck Dean!”

Dean smiled peeking out from between your legs as he moved up to kiss you. 

Donna knocked again. “Y/N. Get your butt up.”

You had rolled Dean over to his back as your mouth was working your way down his torso with open mouth kisses as you were moving down to give him a blowjob. 

”Y/N.” You heard the door jiggle.

You took the cover, throwing it over you and Dean and you licked the main vein, then brought the tip in your mouth, moving down as you began to suck. 

Even though the cover was on, Dean was lost in ecstasy with his hands holding your head when she knocked on the door again. “Y/N?”

“She’s kinda busy Donna,” Dean yelled.

“Oh! OK! Gotcha! Yeah! Send her to the spa when you’re done, OK?”

“OK.” 

She left as you felt him pulsing in your mouth. “Babe…. I’m gonna come.”

Hollowing your cheeks more, he pulsed and released in you. Catching all that you could, you cleaned around him and moved up to kiss him. He began to roll you over slotting between your legs. “I think I need to go.”

Dean smiled and looked at you. “You don’t have enough time for one more orgasm?”

“You know one orgasm will lead to two, then three until I’m exhausted and asleep. Just two more days of this tour and we can spend all day fucking when we get back to the bunker.” You smiled kissing his lips, then pushed him off you, getting up and jumping into the shower to quickly wash off. Throwing on yoga pants and a t-shirt, you pecked Dean’s lips. “See you later Sexy.”

Dean laughed. “I’ll be waiting Baby.”

You were only a half hour late for spa day, which was only a few hours since Donna had a show that night. You had a massage in the same room as Donna, Charlie, Dorothy, and Jody. 

You were on a table that was open for your pregnant belly. As the masseuse, Darren, rubbed your shoulders you seemed to get more uptight. Darren stopped. “Everything OK Y/N. You are getting more tense.” His thick Spanish accent made you think of Antonio Banderas and it was not sexy.

You finally confessed. “I’m not a big into massages.”

“Why?” Donna turned her head to look at you.

“I just don’t. I have never liked them. I relax other ways and Dean knows those ways to help me relax.” You smiled. “In fact, he was helping me relax earlier when you came to get me.”

Jody laughed. “Oh, I bet he does.”

“You betcha.” Donna smiled. “I think he was earlier.”

”Yes he was.”

You got up, leaving the massage room. You then had an organic facial and your hair done because you couldn’t do most of the other things while pregnant. 

When you returned to your room, Dean was gone. There was a note on the dresser. 

** _Sam, Cas, and I went to get something to eat. If you’re hungry, order some food. I’ll be back soon. Love you… Dean._ **

You decided to take a short nap before Donna and Charlie’s interviews later in the day. 

Dean hadn’t returned when it was time to do the interviews. You tried calling Dean’s cell but it went straight to voicemail. 

“He, Cas, and Sam are probably just enjoying themselves.” Charlie looked at you and gave you a hopeful smile. 

“Well, the last time they enjoyed themselves on their own….” Your mind immediately went back to that moment. “Fuck!” You covered your eyes, closing them tight, trying to squeeze the image from your vision and tears formed. “I’m so stupid to believe him.”

Donna hugged you. “Don’t overreact Y/N. I am sure it is not what you think.”

“How do you know?” Tears we’re running down your cheeks.

“I have faith by the way I see him with you.”

Donna and Charlie had their interviews while you stayed on the bus with Dorothy. You kept checking your phone but Dean wasn’t responding. 

** _Are you OK? Please just text me and let me know you’re OK because I am so worried.”_ **

There was no response from Dean. 

Once Donna got on the bus, she texted Dean too but there was still no response. 

When you arrived at the venue, Donna and Charlie went to soundcheck as they were already late. 

You rested in the dressing room looking for Dean sending another text to him, Sam, and Cas. 

** _Dean! It’s Y/N. _ **

** _Sam or Cas - Can you please just have Dean call or text me back. I’m so worried. _ **

_ Dammit Dean! Where are you? _

When Donna and Charlie returned you were curled up in the fetal position on the sofa. “My stomach is cramping.”

“You’re stressed. We need to get you to the doctor. You maybe going into pre labor.” Jody called the ambulance while Donna came over and tried to get you to calm down. “Breathe Y/N.”

You hadn’t been able to take a class on Lamaze breathing, learning online at night on the bus, so you tried the breathing. 

The ambulance arrived, placing you on a gurney and rolled out. After Charlie gave Dorothy a quick kiss, Dorothy went with you since Donna and Charlie were about to take the stage and Jody was head of security. 

You arrived at the hospital in the same pain. It hadn’t increased but hadn’t decreased. You explained why you were in pain and the reason for your stress. You were then hooked up to monitors checking your heart rate and the baby’s and given a mild sedative to relax. The ER doctor came in the room. “We’re going to keep you overnight Ms. Y/L/N to keep an eye on you and your baby. Would you like us to contact anyone for you?”

“No.”

“And what about the father?”

“I’ve tried reaching out to him but he’s not answering.” Your heart rate began to increase.

Dorothy looked at you and back at the doctor. “We’ve contacted everyone that can be contacted at this time.”

“OK. I suggest you just relax. You’re only 29 weeks pregnant so we want to keep your baby in as long as possible.”

“I understand doctor.”

“Get some rest.”

After the show, Donna, Charlie, and Jody came to the hospital to see you and pick up Dorothy but you were asleep. They left a note and told the nurse to let you know they had been there. 


	24. Chapter 24

You awoke in the middle of the night to hear rustling in your room. You opened your eyes to see a Asian looking woman at your IV pole. She didn’t look like the nurse you saw earlier. ”You’re not my nurse.”  


”I’m helping Alesha out.” You looked over at the nurses names and Alesha was the name of your nurse. 

“What’s going on?” You were groggy.

“Just giving you something to help your pregnancy along.” She seemed perturbed you asked.

”I don’t need my pregnancy to come along. I need it to stop.”

”You know what I mean.”

“OK.” You still didn’t trust her. “What is it?”

“Don’t you worry your pretty little head over it.”

That made you sit up and take notice. Nurses are supposed to explain and she wasn’t. Turning on your light, you noticed she was not in scrubs. “Who are you? Why are you not in scrubs?”

Turning to you, she smiled maliciously. “I’m the one he was fucking before you and should be having a baby with. Not you.”

“Oh Fuck! Kim Lee?”

“And you must be Y/N, but not for very long.”

“Why?” You looked at her.

“Because Dean is mine.”

“He doesn’t love you. You rubbed your baby belly and she noticed.

“Here you are; you just dropped into his life, and he just fell for you fast, leaving me behind.”

“It took us months to get together and he said you weren’t together anymore when we met.”

“But he liked you from the beginning.”

“That’s not my fault.”

“But he is mine. I was with him first.” She was getting angry.

You wanted her to see her craziness. “Why do you want to be with someone who doesn’t love you?”

“Well, neither of you need to worry about seeing each other anymore.” Her eyes were dark and menacing. 

“What did you do to him?” You almost spat the words out.

“Dean? Dean is dead sweetie. I already killed him. He kept talking about you and the baby and well, I couldn’t deal with that so I cut his heart out, but I think you should be more worried about what I’m about to do to you.”

“What?” Trying not to panic you tried to stall her. “Please. I just want my baby. I won’t tell anyone.”

”Sure. As soon as I leave, you’ll call security.”

”I promise I won’t.”

”Yeah right.”

Grabbing your IV needle, you ripped it out of your arm, blood beginning to ooze out. You started to get out of the bed, but she grabbed your arm. Knowing she was going to inject you with an air bubble that will cause an aneurysm and then the baby will die of loss of oxygen, you knew you had to think fast. Grabbing your big tumbler of water that you barely drank from, you swung, hitting her hard in the head with your free hand. When she stumbled backwards, you got out of the bed with weak legs and started to fall but held onto the bed remaining upright. 

You took off towards the door but she cut you off. You then stepped back and grabbed a chair and rolled it out in front of her causing her to trip over it. She began screaming at you. “Fuck you bitch.” 

She grabbed the needle from the IV and held it out towards you. 

“Fuck me? Fuck you.” 

You reached out and she swung stabbing you in the arm with the needle. “Ouch!”

Backing up, you pushed the bedside table in front of her, and ran to the bathroom locking the door. Banging on the door, you pulled cord that alerted the nurses station. 

“How can I help you?” 

Breathless, you spoke. “I’m being attacked. I need help. Please.”

Security and nursing staff rushed in subduing Kim Lee. You heard the scuffle. When it finally calmed down, security knocked on your bathroom door. “You OK Miss?”

You stood up, heading towards the door, but you got lightheaded and fell to the floor. 


	25. Chapter 25

You awoke in a hospital bed. Your stomach was still cramping and you were in a lot of pain so you pressed the nurse call button. “May I help you?”

“I’m really hurting right now.”

The nurse came in administering a drug. “You’re having contractions so we’re trying to get them to slow or stop because it’s too early to deliver your baby now.”

“My boyfriend. She said she murdered him. I need to know where he is.”

“The police are here now; I can send them in.”

A policeman and woman stepped in to get your statement. “Miss. Can you tell us what happened?”

“I awoke and she was at my IV pole trying to kill me and my baby.”

“Did you know her?” The police woman looked at you.

“Know of her yes. She was my boyfriend’s ex. She date raped him Tokyo and now was trying to kill me off. She said she killed Dean.”

“Is Dean your boyfriend?” 

“Yes.” 

“When was the last time you saw Dean?”

“Yesterday morning. I went to the spa with my friends. When I returned, he was gone. He left me a note stating him, his brother, and head of security were going to lunch, but they never came back.”

“Head of security?”

“My boyfriend is Dean Winchester.”

The police woman looked at you in awe. “The Dean Winchester, pop star; the one with the hips?” She smiled.

“Yes.” You blushed thinking of Dean’s hips.

“How long have you been together?”

“We were together two months, broke up for three months, got back together and have been together now for a month.”

“Do you know of any reason he would leave you?”

“No. He just told me he loved me just this morning and I’m moving in with him as of tomorrow night.”

“And he was happy with the baby?”  _ Man, that female police officer is really giving me the tenth degree. _

“Yes. He is. He’s already giving him or her cute names.”

“I’ll be right back.” The police woman excused herself and walked away. You saw her talking on her radio. She returned a few minutes later. “I think we’re done here. We’ll let you rest.”

“Please find him, his brother, and friend. I can’t lose him. I love him and he needs to be around for his baby.” You implored. 

“We’ll do the best we can ma’am.”

“Thank you.”

The officers left your room, leaving another officer stationed at your door. The nurse came in giving you another sedative and a dose of the drug to prevent labor. “You need your rest.”

“I just need Dean back.”

“Trust the police are doing the best they can.”

“OK.” You felt your eyes closing.


	26. Chapter 26

Four hours later you awoke feeling like you were being watched. You slowly opened your eyes to see the nursing staff and police officers standing around your bed. You immediately thought bad news.  _ He’s dead. _

“Ms. Y/L/N.”

“Yes.” You were groggy. 

The female officer approached your bed. “We have some news. During the interrogation, Ms. Lee has given us the location of Mr. Winchester, brother, and friend, and we have a swat team going there now.

“Is he OK?” You were almost in tears again. 

“We don’t know yet.” The Officer looked at you.

You were beginning to gasp for air. “I hope he is not dead.” You rubbed your baby. “My baby can’t grow up without a father.”

The officer looked at you with empathy. “We’ll let you know as soon as we hear anything. OK?”

“Yes. Please do.” You were beginning to panic, your heart racing, so the nurse administered another sedative and you went back to sleep.

You were in and out of consciousness all night with nightmares of seeing her face trying to kill you or seeing Dean with his heart ripped out. You woke up screaming at least two times so the nursing staff had to give you a stronger sedative. As you were going under you heard a nurse talking with another nurse. “If we don’t get her under a medically induced coma, she’s going to lose this baby.”

“I know. I’ve called the doctor three times, but he’s just not responding.”

You held your belly, rubbing across your abdomen. _I can’t lose you and Dean in one night. Please God! Just let me sleep. _ Trying to calm your breathing down, you finally fell asleep.


	27. Chapter 27

Around four in the morning, you were greeted by another set of police officers and nurses. “Ms. Y/L/N.”

Groggy again, you looked at them. “Yes.”

“We have good news. We have found Dean. He has been medically checked and…”

“Y/N?”

You looked at the door to see Dean walking in. His face was bruised and cut in many different places, his body looked like he had suffered a lot of beatings. He was draped with a blanket over his clothes as he just released from being seen by a doctor. 

“Dean!” You smiled as you began to sit up. Nurses encouraged you not to get up too quickly and helped you raise your bed. 

Dean walked over and grabbed your hand. “I’m sorry I wasn’t there for you this morning when you came back.”

“I don’t care, Dean, as long as you are back and safe.” You were crying happy tears. 

He leaned in and kissed your lips softly. “I’m glad to be back too Baby. I’m so sorry that she almost…”

“Shhhh. You didn't do anything wrong. It’s not your fault.”

The nursing staff and police were happy to see you reunited. 

Dean stayed the night with you. Even though he had a recliner to sleep in, when the nursing staff left the room, he climbed up into the bed with you, holding you in his arms as one hand pressed against your abdomen. As you fell asleep, you heard him talking. “I don’t want to lose you or the baby.” 


	28. Chapter 28

After a week of keeping you from premature labor, you were allowed to head home. Dean bought a van with a bed in the back so you could stay on mandatory bed rest as he drove back to Lebanon. He took the long way home, stopping throughout the four day trip, sleeping in the van with you at rest stops.

When you got back to the bunker, you had no clothes but what you packed while on tour with Donna and Charlie, so Dean told you to buy what you needed online and paid for it all. You got clothes, shoes, toiletries, and baby things. 

Dean and Sam quickly busted out walls next to your shared room to create a nursery and got it furnished for your little one.

You were in week thirty four of your pregnancy by then and on mandatory bed rest, which was not fun, but when not in his studio writing or recording, Dean stayed in bed next to you and watched TV and movies on his 80 inch bedroom TV. He was able to get all the channels and on demand movies you or he would ever want which filled out all your time; however, you were obsessed with a little genre Sci fi show called Supernatural and binged watched it all day. You were attracted to one of the main characters who was also named Dean Winchester played by Jensen Ackles, and looked just like Dean, which made Dean uncomfortable. 

You smiled. “He looks just like you.” 

“You think?” Dean tilted his head. “I don’t see a resemblance.”

“Of course I think he does. You could be identical twins.” You smiled. “He’s also fucking hot!”

“What? If he’s hot, what am I, chopped liver?”

“No. You’re even more gorgeous and hotter too.” You smiled as you touched Dean’s chest.

“But if we look the same, how am I hotter?”

“Because I know your soul Dean and it is far more gorgeous.”

“Can he give you multiple orgasms?” Dean smirked. 

“I don’t know. Maybe I should find out. I should search this guy out.” You pretended to climb out of bed. Dean pouted, grabbing your hand, so you stroked his ego and pride. “You know you’re the only man I want.” You reached your hand down the waistband of his jeans and gripped his hard cock, stroking it slowly. 

“You’re just saying that.” Dean’s breath hitched.

“We’re having a fucking baby together. I’m not just saying that.” You leaned in and nibbled his ear as you began to stroke him faster. 

“OK babe. Whatever.”

You then moved to his lips and kissed him passionately, stroking him faster. “God, I love your cock in my hand.”

Dean started to pant as you continued to stroke him, feeling him pulse around your hand, finally releasing thick ropes in your hand. 

Raising your hand to your mouth, you licked the salty sweet of him off you. Dean grabbed your mouth kissing you as he tasted himself on your tongue.

Being on mandatory bed rest also meant no intercourse for you, which killed Dean more than it killed you; however you kept him satisfied as you could still give him blowjobs (if you weren’t nauseous) and hand jobs. 

———————————————————

Seven weeks later at forty one weeks, you were angry and pissed your child had not been born yet. Doctor gave you the go ahead for sex or anything that would help induce labor and Dean was on that train from the getgo. Dean quickly drove you back from the doctor and you both walked into the bunker.

“Hey Y/N. How are you doing?” Sam smiled sitting at one of the tables looking at his laptop. 

“Stick a fork in me!” Your bitch face meant you were in no mood to smile.

“Fork?” Cas looks confused.

You shook your head and growled. “I’m done.” 

Cas tilted his head and looked at you like a dog when you ask a question.

Sam could see you were in no mood to explain what ‘stick a fork in me, I’m done’ reference meant. “I’ll explain it to him.” 

Dean smiled at Sam. “Thanks. By the way, you may want to check out of here for awhile.”

Cas looked confused again. 

“I’m on baby inducing duty.” Dean smirked. Sam immediately understood. “Ew! OK.” 

Cas looked confused again. 

“Go on. Help her get that baby out.” Sam laughed. “Hey Cas. Let’s go to lunch.”

“OK.” Cas followed Sam out the bunker, and Dean began to follow you towards the bedroom. 

You were pulling clothes off right and left, leaving them on the floor leading Dean on a path. He did the same, removing articles of clothing where you left one. As he approached the bedroom door, the last article of clothing, your panties, laid on the floor. Dean removed his boxers and opened the door. “Hey Baby.”

You were lying across the bed with a sheet covering you while Dean walked in naked. “This is completely unfair babe. Here I am naked, just letting everything hang loose, and you’re covered with a sheet.”

“You can come over here and share my sheet with me if you want.” You smirked. 

He walked over and you opened the sheet enough for him to slip in, but he lifted the sheet higher as you tried to pull it back down. “You’re beautiful. You don’t need to hide.” Dean smiled.

“I’m a beached whale Dean.”

“Then I’m Greenpeace sweetheart. I’m here to save the whales.” He smiled and you chuckled with him. 

He leaned in and kissed you, setting a fire to your belly. Staying on your sides, your kisses got hungrier as your hands roamed each other’s bodies. “I miss this.” You felt Dean pulling you closer. 

“Me too. It’s been so long baby.”

“I need you.” 

Hands got needier as he first began to knead your breasts, and you moaned. He slowly moved his hand down your torso, waist and hips, squeezing your buttocks. “Please Dean.”

Moving his hand back around, he slipped his hand down between your legs and began to massage your clit. The noises and moans you began making indicated that you liked what he was doing. 

“You like that, don’t you sweetheart?”

“Oh God Yes. More Dean.”

Slipping your hand down, you stroked his erection, and Dean’s grunts indicated he liked what you were doing to him too. 

He continued as you began to clench around nothing. Slipping his hand down further, he started opening you up by slipping one, then two fingers in you. 

“Oh God Dean. Yes!” It didn’t take long for your first orgasm to hit as he was getting close to exploding with you stroking him. “I need you in me Dean. Please.”

Keeping your top knee straight and to the side, Dean slid his leg over yours, pushing himself inside you at a new angle. You cried out, loving what he was doing to you. “Yes!”

“You feel amazing baby.”

He continued thrusting in and out of you. “More Dean!”

No matter what he tried, he couldn’t get you to orgasm. Finally, he pulled out of you and rolled to his back. “Ride me Baby.”

Straddling his hips, you lined his cock to your entrance and lowered yourself on him. Starting at a slow pace, you undulated your hips, working up to a faster pace. You were swearing, wishing for a miracle, praying to a god you don’t believe in. You whined, waiting for your world to explode. “Please! Please! Please!”

Dean held onto your waist with a brutal grip as his hips met yours, thrusting into you, until you finally viced around him and your eyes were consumed with flashes of light. “Yes! Oh God Yes!”

Dean grunted as he released in you. You circled your hips as you worked through your orgasm. He rolled you to your sides as you captured his lips in a passionate kiss. He pulled out of you, so you got up and headed towards the bathroom. After doing your business and cleaning yourself up, you began walking back to bed when you stopped, feeling the water breaking and gush below. “I think my water just broke.” Doubling over, you had your first contraction.

Dean was up immediately throwing on jeans and a t-shirt. He helped you put on a long dress as you already began having contractions. He grabbed your overnight bag, wrote a quick note to Sam and Cas, and helped you out to the car.

When you reached the hospital, as soon as the nursing staff saw Dean, they were swooning all over him asking for autographs. You stood there in pain, falling to the floor interjecting. “Excuse me. I need help here.”

Dean looked up and immediately came over to you, holding your hand as another contraction ripped through you. Someone grabbed a wheelchair and Dean helped you into it as they pushed you to Delivery. 

After Thirteen painful hours of labor, you delivered a beautiful baby girl. Dean swiped your sweat soaked face. “You did it baby. You did it.”

Dean cut the umbilical cord and the nurse set the baby in your arms. You looked over at Dean and down at your little girl. She looked like Dean’s mom. “She’s beautiful.” 

Dean smiled. “She looks like her mom… beautiful.” You began to cry that Dean saw you in your daughter, but you saw his family. He leaned in and kissed your lips tenderly. 

You fell back against the pillow. “I’m so tired.”

“Sleep baby. I’ll be right here.” You looked at Dean smiling as your eyes slowly closed.


	29. Chapter 29

Returning to your home, the bunker, you brought your daughter, Deanna Leeann, named after her father and great grandmother and your mother’s middle name as her middle name. 

Dean was a wonderful father. He helped with the diaper changes and feedings when you were too exhausted to move and couldn’t breastfeed. He was constantly singing to you and his little one helping her fall asleep. Sam and Cas were great uncles and enjoyed caring for little Dee Dee when needed. 

At six weeks, you had your checkup and talked to your doctor about how your libido coming back and when you could have sex again. He stated it was up to you when you felt good enough for sex. 

When you returned to the bunker, Cas was watching Dee Dee sleeping, rocking in her rocking seat. “Where’s Dean?”

“He’s in his studio. How are you feeling?”

“Great.”

“That’s good.”

You looked at Cas. “Hey! Do you mind watching Dee Dee for a few more hours?”

“No Y/N. I don’t mind, but what if she cries.”

“She may need a bottle or changed. Diapers are in the nursery and breast milk is in the fridge. is Sam here?”

“He’s out for a run. He’ll be back soon.”

“Maybe he can help.”

“OK.”

“If you need anything, TEXT Dean or I. Don’t come into the studio.”

“OK.”

“Thanks Cas.”

You walked towards to your room, undressed and put on your robe. Walking to the studio, you heard Dean recording a chorus on a piano. “I love you baby girl, and I always will, I have loved you before you were born, you beautiful child.”

You began to cry. This was the lullaby’s has been singing and is recording it. 

He then switches gears and starts a sexy riff on his acoustic guitar. “My beautiful woman, I love you so much, I need to be with you. I need to feel your touch.” 

You walked up to the glass studio door and knocked. It took a few minutes for Dean to answer. “Hey!” He smiled and you smiled back.

“Hey Dean.”

“Are those new songs?”

“Yeah! One is called ‘My Baby Girl’ for our baby and the other is called ‘My Beautiful Woman’ for you.”

“Thank you Dean. They sound beautiful. Did you save the recording?”

“Of course.” He smiled. “So, how did the doctor’s appointment go?”

“Really well Dean. Really well.” Your smile widened.

Dean looked at you. You wiggled your eyebrows at him. “Oh. That good.”

You threw your arms around his neck, kissing him, pushing him inside the studio, shut the door, and closed the blinds. You pushed him back to a chair and he sat. Undoing the ties of your robe, you let it open, falling off your shoulders, and dropping to the ground.

Dean looked at you completely naked. You had stretch marks on your stomach and breasts and felt inadequate for such an attractive man as he is, but he then smiled. “You are so beautiful sweetheart.”

You leaned down and kissed him passionately, straddling, then sitting on his lap facing him. “Dean.”

“What baby.”

“It’s been six weeks and I really need you.”

“I’m here sweetheart. Whatever you need.”

You held his face as he looked up with you in love and admiration. “I need you inside. I need fucked good and hard.”

”I’m here for you. Lead the way baby.”

After a long, passionate kiss, you pulled off his flannel shirt and slipped your hands under the hem of his shirt, feeling his hot skin as you pulled it up and off of him. His hands ran up and down your torso, around your breasts as his lips moved from your neck down to a breast. His lips and tongue worked the nipple until it was hard. Popping the button and unzipping his jeans, your hands skimmed underneath the waistband as his tongue and lips worked the other nipple. “Oh man. I miss this baby.”

“Miss you too Dean.” You slid off his lap, down to your knees. As he lifted his buttocks off the chair, you pulled his jeans and boxers down his legs and off. You ran your your hands up and down his thighs. “I love watching you expand in front of me; letting me know how much you want me.”

“Of course I want you baby.”

You leaned down and kissed his inner thighs. “You’re so gorgeous Dean. I love watching your cock react to me.” You saw his cock twitch in front of you. “You ready for me.”

Dean’s breath hitched. “Of course babe.” 

You leaned down licking the main vein, hearing Dean grunt. Licking around the shaft, you took him in slowly, inch by inch until he hit the back of your throat. Reaching down, squeezing his balls, and holding onto one thigh, you began to suck. He ran his hands up and down your back while he praised and encouraged you, as you worked him in your mouth. “I love your mouth on my cock. I love the feeling of you sucking me off. So good sweetheart. There. OK. A little faster.” You went faster as his hands moved up, grasping both sides of your head as he began to thrust, getting close, pulsing around you. Squeezing his balls just enough, he came with a groan as he filled you with thick ropes that you swallowed down, then you cleaned around him, letting him go with a pop and looked up at him with lidded eyes. “Come here baby.” You moved up, straddling his legs again as you kissed him, letting him taste him on his tongue. 

“Your turn baby.” He got up, holding you in his arms, turning around and smiling. He had you sit in the chair moving it up to the sound board then had you prop your spread legs on the edge. He started slowly kissing down your torso, to your inner thighs. You squealed in ecstasy at the first time his tongue ran up your slit; it had been so long since you had been touched by Dean that you immediately reacted. “Oh Fuck! This feels amazing.”

He did it again, then latched on to your clit and sucked as he started thrusting one, then two fingers to your entrance.

“Fuck! Yes! Oh Fuck! Yes. Please!” You were writhing against Dean’s face, cursing everything around you as he ate you out like a starved man. 

“Fuck! You taste so good.” 

He continued to work you over and it didn’t take you long to feel your body clenching around him as your orgasm blinded you in white light and you wailed in ecstasy. Dean peeked up at you sheened in your arousal, then pulled you into his arms, kissing you. Turning you both around, he sat down as you his waist, sitting down, being impaled by his newly formed erection. 

Undulating your hips, you started the pace as Dean wrapped an arm around you while the other hand kneaded one breast while his mouth puckered around the other breast. 

“Oh Fuck! Yes!” You we’re bouncing hard on Dean’s cock; your hand reached down between your legs to massage your clit. “Oh shit! Please!”

Dean began to get rough, grabbing your hips as he thrusted up into you. “Fuck baby. You feel so good.” He stood up tossing you on the sound board as he rammed into you, getting the angle needed to hit your g-spot. 

You were screaming Dean’s name like you were being murdered. Your entire insides felt like a pinball machine as little shocks hit your overstimulated core with each thrust causing you to finally vice around Dean’s cock, seeing white. 

At your last screaming exhale, you felt Dean fill you up, as he howled, then leaned in and kissed you. 

Sweating and panting, you opened your eyes and saw Dean’s face looked sad. “I’m sorry baby. I got way too rough.”

You laughed. “Dean.” You touched his face and made him look into your eyes. “It’s OK. Really. Fuck! I missed you inside me.”

“You sure sweetheart.”

You rolled your hips and could feel the twinges off his erection coming back in. “Stay in me Dean.”

“Sure baby.” He picked you up carrying you over to the sofa, as he lowered you down on it. Rolling to to your sides, he kissed you passionately. “You feel so good baby.” 

“You too my honeybear.”

You rolled your hips until Dean’s erection was back as he made sweet love to you on the sofa, rocking into you until he filled you up again. “I love you.” You looked up into his eyes as you held his face in your hands. 

“I love you too.”


	30. Chapter 30

Ten months later, you were at the Grammy Awards where Dean was up for Song of the Year for “Because of You”, album of the year for “My baby girl”, and Pop song of the year for “My Beautiful Woman.” He was in a dark maroon tux and you in a long black dress with a sweetheart neckline and tight curves with your nine month baby bump proudly showing. Your daughter stayed with Sam that night as this will probably one of your last date nights for quite awhile with soon to be two kids. 

You walked the red carpet behind Dean, holding his hand, letting him have his moment in the limelight. Dean smiled, smoldered, and smirked for the cameras, his model, yet ruggedly good looks made the cameras love him. His long bow legs, nice ass, strong arms, and pecs made him look amazing in anything he wore. 

“Dean! Dean!” The paparazzi was calling out his name. Dean smiled, sticking his hand in his pocket or pretending to look at his watch, whatever they asked him to do. 

Dean grabbed your hand as you continued to walk down the carpet. “Dean. Who’s with you?”

Dean smiled. “This is my lovely lady and the inspiration for ‘Because of You’, ‘My Baby Girl’, and ‘My Beautiful Woman’.”

“Give us a picture you two.” Dean pulled you close to him, his hand on your back, as you smiled nervously. The photographer saw your pregnancy. “When are you due?”

Dean placed his hand on your stomach. “Any day now.” Dean smiled like a proud papa.

The paparazzi looked at you.“How are you feeling about Dean’s nominations?”

“I’m extremely proud of him, and he’s already won in my book.” You had joyous tears in your eyes.

Dean smiled as he leaned in and kissed your lips tenderly. At that moment you only felt Dean’s lips, no crowds, as you moved your lips with him. Finally coming out of your head you blushed as the photographers were all around you taking pics of Dean and you kissing. 

You made it into the theater; you and Dean were put in the aisle of the third row next to the band matchbox twenty. You were fans of matchbox twenty for a long time. They even remembered you, so you introduced them to Dean. ”This is Rob Thomas. Rob, this is my boyfriend Dean Winchester. You two should write together.”

Rob Thomas smiled. “Yeah Man. Call me.” He gave Dean his cell number. 

Dean smiles. “Thanks. I will.”

You sat down, looking across the aisle, and gasped. It was Jensen Ackles with his band, Radio Company. You whispered, “Dean! It’s your doppelganger.” 

“Huh.” He looked over and saw Mr. Ackles sitting across from aisle from you. 

“I’m going to go talk to him.” You smiled. The show hadn’t started yet. Dean got up letting you past and you walked over. “Excuse me. Mr. Ackles.”

“Yes.” He looked over at you and you could have sworn Dean switched places with him; his green eyes pierced yours. You swallowed. “Hi. I’m Y/N and I’m a big fan of you and your show. I watch it all the time. I’m sad it’s ending.”

Jensen stood up and you shook his hand. “Glad you like the show.”

“You see my boyfriend is a singer whose name is the same character name you play on the show, Dean Winchester. Dean. Stand up.”

Dean stood up and walked over putting his arm on your back. You thought you were looking at a split screen. They eyed each other up and down and even Jensen’s wife, Danneel, looked at him shocked and said, “he looks just like my husband.”

“I know.” You smiled. 

You decided to take some pictures. First the four of you took photos together. Then you took pictures with Jensen and Danneel with Dean, just to throw people off. You hugged Jensen. “Thanks for making the best character on television. I’m going to miss him.”

“You’re welcome, and I will too.”  


You turned around. “You should collaborate on something together.”

Dean smiled. “Sure.”

Jensen smiled. “Sure.”   
  
They both smiled. They had the same mannerisms. You finally sat back down as the show was about to begin. Grabbing Dean’s hand and interlocking fingers, you watched as the show began. 

The performances were great. You loved Panic! At the Disco as Brendan Urie is so much fun. Radio Company’s performance was great and you smiled looking at the man who looks like your man singing. Dean had to leave to go backstage as he was performing shortly and seemed to be getting nervous. He was going to sing a medley of his three nominated songs. You pecked his lips and squeezed his hand before he left. You sat there as a seat filler came and sat next to you.

Dean took stage with just an acoustic guitar. He nervously grabbed the mic and smiled. “These are for the loves of my life, Y/N, and my baby girl, Dee Dee. I love you.” He began to sing and by the end of the medley, there was not a dry eye in sight. The entire theater gave Dean a standing ovation including you as you smiled and cried, clapping excitedly. 

Dean returned to his chair and you grabbed his hand as his awards were coming up. 

Jensen Ackles was the one who was giving out the Pop Song of the year and you began to laugh when you thought about Dean and Jensen on the stage together. “And the winner of Pop Song of the Year goes to…. Dean Winchester.”

Dean stood up shocked. He leaned in and kissed you, then walked up on the stage and shook Jensen’s hand, taking his award. After the photographers and celebrities had a hay day with the lookalikes, he made his acceptance speech. “Thank you Heaven Sent Records, Chuck Shirley, my band, my brother Sam, my best friend and head of security Castiel, but mostly the woman that inspired me to make these three songs. Y/N. I love you.”

You were crying so hard, happy tears. When Dean returned you kissed his cheek and couldn’t stop smiling. 

Song of the Year was a next and Kelly Clarkson was the one to announce. “The Grammy goes to...Dean Winchester.” 

Dean got up again and went up to accept the award. Thanking most of the same people, he again looked your way. “Y/N! You have given me the best year of my life and I will always be eternally grateful. Thank you.”

After the interviews, he returned back to his seat and the last award was up. Taylor Swift was announcing the last award. “The Grammy goes to… Dean Winchester.” Dean got up and turned around. “Will you come up there with me?”

You looked around embarrassed. You began to shake your head nervously. “Me?” 

“Come on. I got you.”

He put his arm around you as he helped you up the steps. Taylor hugged Dean then you and you stood back. 

“I brought this beautiful woman up with me tonight because there isn’t anymore more I can say to her and thank her for the last year except for this.” Reaching in his pocket, he pulled out something and got down on one knee as he looked at you. “You didn’t like me much when we met. I was a womanizing asshole who spent more time wanting to get into a woman’s pants than get to know her. You changed that in me. You made me want to learn more about you. Then there was Venice and everything changed. I was in love with you by then, we conceived a beautiful baby girl. You stood by me during one of the worst things that has ever happened to me and more importantly to you, but you learned to love me again and stuck by me. Now we have our beautiful baby girl and you’re ready for our next bundle of joy. I think it’s time we make things official. Y/N. Will you marry me?” Dean opened a box and presented a beautiful platinum ring to you. He looked at you hopeful, waiting for your response. 

You began to cry as you looked at Dean asking you to marry you at an awards show, in front of everyone. He loves you and you love him. “Yes Dean. I’ll marry you.” He stood up, pressing his hands to your cheeks and kissed you passionately while the crowd gave him a standing ovation. When he pulled away, you looked nervously at the crowd. You smiled as Dean grabbed your hand and raised his award in his other hand and yelled. “She said yes!”

You were still onstage heading towards backstage when you felt pain in your abdomen, then looked down as your water broke, gushing on the stage. “Dean. My water just broke.”

“Shit!! OK. Don’t panic.”

“I’m not panicking.” You laughed. 

“OK. I got you.” He picked you up bridal style and carried you backstage. There was already an ambulance for emergencies and you were now the emergency. He helped you in the ambulance then climbed in as he held your hand.

You reached the hospital to deliver another daughter only an hour later. She was named Samantha Cassidy after her Uncle Sam and Uncle Cas.

You were then married three months later in a small ceremony on the beach in the Caribbean. All your friends and family was there: Sam brought Eileen, an old friend that he reacquainted with; Castiel brought your friend Belinda from Australia; Donna and Doug, Charlie and Dorothy arrived; and Jody brought a new man with her. 

As you stood on the beach with your toes in the sand, the minister saying “you may now kiss the bride,” Dean leaned in and kissed you passionately. Everyone clapped and you had the reception on the beach. 

At the end of the night, you and Dean had slipped away from the party, going to a rocky part of the beach where Dean laid down blankets and made love to you in the sand. As you laid in his arms after and thought about your life up to this point, you couldn’t believe that all this happened from a world tour. 

The End. 

**Author's Note:**

> More to come. 
> 
> Thanks for reading.  
Please comment if you like. Kudos welcomed and appreciated.  
I know I’m not the world’s best writer but I try.  
If you like the story, let me know. I like to know if I’m at least doing something right.  
If you don’t like the sorry, that’s OK but please don’t be a dick about it. Just move on. 
> 
> Do not copy or disseminate this work in any other public or private form without the express written consent of the author.


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